Phosphoric Acid Catalyzed Formation of Hydrogen-Bonded o-Quinone Methides. Enantioselective Cycloaddition with β-Dicarbonyl Compounds toward Benzannulated Oxygen Heterocycles

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Article

Phosphoric Acid-Catalyzed Formation of Hydrogen-Bonded

ortho-Quinone Methides. Enantioselective Cycloaddition with #-

Dicarbonyl Compounds toward Benzannulated Oxygen Heterocycles

Fabian Göricke, Stefan Haseloff, Michael Laue, Maximilian

Schneider, Thomas Brumme, and Christoph Schneider

J. Org. Chem., Just Accepted Manuscript • DOI: 10.1021/acs.joc.0c01375 • Publication Date (Web): 10 Aug 2020

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The Journal of Organic Chemistry

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The Journal of Organic Chemistry

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E\FDGDE9DS68*8FDJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61, E+,-jW

0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: Kgm icYWO 9Dj !1 !

'8+⁹⁰

%*$*'!2 T'3(*:7'* /3' ]$!$.#31*2*(.#F* A::#.#3$ 3/ N+OR

>P(235*8!$*:#3$*W

S5#.* 132#:+ *' KJWcogWc+

q Rccn i( q NWL+ >0>2_Oj+ 9? q

;

NMd R NcLn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJN Ä YWKY

i9+ d0j+ cWLO i1+ N0j+ JWgK Ä JWcc i9+ J0j+ JWMg Ä JWOL i9+

J0j+ JWJc i1+ O0j+ JWNN Ä NWKO i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL

40H+ >X>2_Oj Ñ ^??9` q NKgWN+ NYYWJ+ NMKWY+ NMOWc+ NOYWL+

NOLWLN NJKWO+ NJgWK+ NJgWg+ NJcWd+ NJcWJ+ NNYWY+ NNcWL+ OgWc+

$.-26R5P:'38P "*$HP2 !2(3532 & iLWJ 9932+ NWL *[7#FWj+ N+OR

(P(235*8!$*:#3$* '( iOOWY 9D+ LWOL 9932+ NWc *[7#FWj !$:

(!.!2P1. E iYWg 9D+ LWLN 9932+ c 932 mj S*'* :#1132F*: #$

(523'3/3'9 iNWY 96j !. \;+ NLn> 3' Ln>W ;5* '*!(.#3$

9#8.7'* S!1 1.#''*: /3' NRJ :!P1 !. .5* 1!9* .*9?*'!.7'*

7$.#2 (39?2*.* (3$179?.#3$ 3/ .5* 1.!'.#$D 9!.*'#!2W ;5*$

9D.327*$*172/3$#( !(#: 93$35P:'!.* igWY 9D+ LWLM 9932+

JL 932mj S!1 !::*: !$: .5* '*!(.#3$ 9#8.7'* S!1 /7'.5*'

1.#''*: /3' M 5 !. MLn>W ;5* ('7:* '*!(.#3$ 9#8.7'* S!1

?7'#/#*: "P 153'. /2!15 (5'39!.3D'!?5P i5*8!$*t4;<] KoNj

.3 !//3': .5* :*1#'*: 8!$.5*$3$*1W ;5* *$!$.#39*'#( '!.#31

S*'* :*.*'9#$*: "P 0T6> 3$ ! (5#'!2 1.!.#3$!'P ?5!1*W

9

^(9^RN` q NYYN+ NYMM+

<

OgWJ+ JdWL+ JNWJ+ JLWc+ A\ ib<'j

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NYNN+ NMdY+ NMcd+ NOgY+ NJOK+ NJJJ+ NJLO+ NNgK+ NNcg+

NNOL+ KKM+ dJO+ gJJ+ YMJ+ cJY+ 0\R4- i]-Ajo (!2(W /3'o

i^4_Z!`^_jo ONOWNNKKá /37$:o ONOWNNKg+ 0T6> CX0 >3279$

iKcm 5*8!$*o cm /R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq KWc

9#$ !$: \_.Jq NLWg 9#$W

E\FDGDEHDT.69*892,1*8FDJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD

61, E+,.jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: dKm icYWg

'8+⁹⁼

E\FDGDEHDI,-26:*92,1*8FDJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD

61, E+,,FN 0*8!$*t4;<] iKoNj !1 *27*$.+ Kc m P#*2: icdWJ

'8+^9:

9Dj !1 ! S5#.* 132#:+ *' KJod+

q RMLn i( q NWL+ >0>2_Oj+ 9?

;

q gN R gcn>+ ^N0 Z4\ iOLL 40H+ >X>2_Oj Ñ ^??9` q gWJM Ä YWKY

i9+ d0j+ cWLM i1+ N0j+ JWdN Ä JWcg i9+ J0j+ JWcM Ä JWMY i9+

J0j+ JWMc Ä JWJd i9+ J0j+ JWNN Ä NWKM i9+ J0j+ NWYY Ä NWcL i9+

J0j+ LWKN i.+ A q gWO 0H+ O0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj

Ñ ^??9` q NKgWN+ NYYWO+ NMKWY+ NMOWY+ NMLWg+ NOLWJ+ NJdWY+

NJgWd+ NJgWY+ NJcWd+ NJcWN+ NNYWc+ NNcWN+ OgWd+ OgWc+ OgWN+

9Dj+ !1 ! S5#.* 132#:+ *' Kcoc+

q ÄcMn i( q NWL+ >0>2_Oj+

;

9? q NNO R NNYn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJN

R YWKK i9+ Y0j+ YWdY R YWYc i9+ J0j+ cWLJ i1+ N0j+ OWgO i1+ O0j+

JWdL R JWcK i9+ J0j+ JWMc R JWON i9+ J0j+ JWNg R NWKJ i9+ J0j+

^NO>Ö^N0Ü Z4\ iNLL40H+ >X>2_Oj Ñ ^??9` q NKgWJ+ NYYWN+

NcdWN+ NMKWY+ NOdWd+ NOLWO+ NJKWL+ NJgWY+ NJcWd+ NJcWJ+ NNYWc+

JdWL+ JMWc+ JLWc+ NMWN+ A\ ib<'j

^(9^RN` q JKcc+ JKJK+

NNcWN+ NNOWK+ ccWO+ OgWJ+ OgWL+ JdWL+ JLWc+ A\ ib<'j

^(9^RN`

<

JdYd+ NYMJ+ NcdL+ NcNL+ NMdY+ NMcc+ NOgc+ NJOd+ NNgK+

NNOL+ KKc+ KNK+ gcM+ YLO+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo

OMNWNcNdá /37$:o OMNWNccJ+ 0T6> A< >3279$ iKcm 5*8!$*o

cm /R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq gWY 9#$ !$: \_.Jq

dWM 9#$W

q OLON+ OLNO+ JKcO+ JdKK+ JdOc+ NYWcd+ NYML+ NYNJ+ NcdJ+

NcLK+ NMdg+ NMcd+ NOgc+ NJYL+ NJMO+ NJJO+ NNdN+ NNgJ+

NNJd+ NLOL+ KKY+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo

OJKWNNcMá /37$:o OJKWNNMd+ 0T6>% CX0 >3279$ iKcm

5*8!$*o cm /R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NcWN 9#$

!$: \_.Jq NdWY 9#$W

E\FDGDEHDU846.692,1*8FDJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD

61, E+,/jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: KJm icMWJ

'8+^9:

E\FDGDEHDE.*'.DO4-*8F92,1*8FDJKLKHKGD-,-.32*5.6DM;D:31-2,1D

MD61, E+,'FN 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: KJm iYNWJ

'8+^9:

9Dj !1 ! S5#.* 132#:+ *' KdoJ+

q ÄgOn i( q LWMN+ >0>2_Oj+

;

9? q NLd R NNLn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJO

Ä gWNc i9+ O0j+ gWNJ Ä gWLL i9+ O0j+ YWKY Ä YWdc i9+ J0j+ cWLc

i1+ L0j+ JWdL Ä JWcc i9+ J0j+ JWcL Ä JWOL i9+ J0j+ JWNc Ä NWKJ

i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKgWN+

9Dj !1 ! S5#.* 132#:+ *' Kcoc+

q RMJn i( q NWL+ >0>2_Oj+ 9?

;

q cL R cOn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJM R gWJL

i9+ J0j+ gWJL R gWNL i9+ M0j+ gWNL R gWLL i9+ J0j+ cWLc i1+ N0j+

JWdJ R JWcc i9+ J0j+ JWcJ R JWJM i9+ J0j+ JWNY R NWKL i9+ J0j+

NWJc i1+ K0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKgWJ+

NYYWM+ NMKWg+ NMKWL+ NMOWJ+ NOLWJ+ NJgWY+ NJgWc+ NJcWd+ NJcWM+

NJcWN+ NNYWc+ NNcWN+ OgWM+ OgWJ+ OMWc+ ONWc+ JdWN+ JLWc+ A\

N

NYYWM+ NYNWc i:+ A_>Rq JMMWc 0Hj+ NMKWc+ NMJWNd+ NMJWNc+

NOLWN+ NJKWY i:+ ^OA_>Rq dWL 0Hj+ NJgWK+ NJcWO+ NNYWg+ NNcWO i:+

J

<

A_>Rq JNWO 0Hj+ NNMWd+ OgWJ+ OgWN+ JdWL+ JLWc+ A\ ib<'j

^(9^RN` q OLgN+ OLMJ+ OLNc+ JKYL+ JKOY+ JdKO+ JdgY+ NYcY+

NYLL+ NcdL+ NcLY+ NOgc+ NJOg+ NNgg+ KKg+ dMc+ gcM+ 0\R4-

i]-Ajo (!2(W /3'o i^4_Z!`^_jo ONgWLKcMá /37$:o ONgWLKMd+

0T6> CX0 >3279$ iKcm 5*8!$*o cm /R?'3?!$32+ N 96t9#$+

JgL $9j \_.Nq KWg 9#$ !$: \_.Jq NNWO 9#$W

ib<'j

^(9^RN` q OLMM+ OLJY+ JKYL+ JKLN+ JdYd+ NYYO+

<

NYMY+ NYOK+ NYNO+ NcdN+ NMdc+ NMcY+ NOgc+ NJOY+ NNgg+

NNOJ+ KKM+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo OccWNYgMá

/37$:o OccWNYYd+ 0T6> CX0 >3279$ iKcm 5*8!$*o cm /R

?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq dWJ 9#$ !$: \_.Jq KWY 9#$W

E\FDGDEHDO.6+692,1*8FDJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD

61, E+,0jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: gKm icYWN

'8+⁹⁰

9? q NNK R NJNn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWOd

Ä gWOL i9+ J0j+ gWJO Ä gWNc i9+ N0j+ gWNM Ä gWLN i9+ c0j+ cWLO

i1+ N0j+ JWdL Ä JWcd i9+ J0j+ JWMd Ä JWOL i9+ J0j+ JWNM Ä NWKL

i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKgWL+

NYYWc+ NMKWc+ NMcWO+ NONWY+ NOLWN+ NJKWK+ NJdWL+ NJcWO+ NJMWd+

E\FDGDEPMKMQDO/92,1*8RDHD*8FDJKLKHKGD-,-.32*5.6DM;D:31-2,1D

MD61, E+,(jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: KNm iYMWN

'8+⁹⁰

q NYK R NgNn>+ 0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWcM Ä

gWMd i9+ J0j+ gWMd Ä gWMJ i9+ J0j+ gWMJ Ä gWOc i9+ J0j+ gWOM

Ä gWJg i9+ O0j+ gWJO Ä gWLJ i9+ M0j+ cWNJ i1+ N0j+ JWdJ Ä JWcK

i9+ J0j+ JWcL Ä JWOJ i9+ J0j+ JWNc Ä NWKc i9+ J0j+ ^NO>Ö^N0Ü

Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKgWJ+ NYYWc+ NMKWY+ NMcWM+

NMNWN+ NOKWM+ NOLWJ+ NJdWd+ NJdWM+ NJgWd+ NJgWO+ NJgWJ+ NJcWM+

9Dj !1 ! S5#.* 132#:+ *' KOog+

q ÄJLn i( q JWY+ >0>2_Oj+

;

9Dj !1 ! S5#.* 132#:+ *' KMoY+

q Rdn i( q NWL+ >0>2_Oj+ 9?

;

N

^(9^R

<

NJLWM+ NNYWg+ NNMWc+ OgWc+ OgWN+ JdWL+ JLWc+ A\ ib<'j

^N` q NYcK+ NYMM+ NcdN+ NMdc+ NMcc+ NOgM+ NJOd+ NNgc+ NNOL+

NLgL+ NLNL+ KKM+ dMO+ gcg+ cJY+ 0\R4- i]-Ajo (!2(W /3'o

NJcWO+ NNYWg+ NNMWd+ OgWY+ OgWJ+ JdWN+ JLWc+ A\ ib<'j

^(9^R

<

^N` qOLcg+ OLcM+ OLJg+ JKMM+ JdKM+ NYYL+ NYOK+ NcgK+ NMdc+

NOgM+ NJOY+ NJJY+ NNgg+ NNON+ KKY+ gcd+ 0\R4- i]-Ajo (!2(W

/3'o i^4_Z!`^_jo OgcWNOYNá /37$:o OgcWNOcY+ 0T6> CX0

i^4_Z!`^_jo

OggWLNdNtOgKWLNdNá

/37$:o

OggWLNMYtOgKWLNMY+ 0T6> CX0 >3279$ iKcm 5*8!$*o cm

ACS Paragon Plus Environment

The Journal of Organic Chemistry

Page 14 of 26

/R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NNWM 9#$ !$: \_.Jq NOWO Ncdg+ NMKL+ NMcc+ NOgc+ NJcO+ NJJO+ NJNO+ NJLJ+ NNKL+

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9#$W

NNON+ KKY+ dJd+ gLL+ YKL+ cOL+ 0\R4- i]-Ajo (!2(W /3'o

i^4_Z!`^_jo ONOWNNKKá /37$:o ONOWNNKK+ 0T6>o CX0 >3279$

iKcm 5*8!$*o cm /R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq gWKc

9#$ !$: \_.Jq KWLO 9#$W

E\FDI,-2*8DHDEMD6:6DJKLKHKGD-,-.32*5.6DM;D:31-2,1DGD

*8F>,1C63-, E+,%jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: gLm

'8+⁹_;⁼

iMYWd 9Dj !1 ! S5#.* 132#:+ *' KOog+

q _Mn i( q NWL+

>0>2_Oj+ 9? q NgN R NgOn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9`

q gWKO Ä gWdY i9+ J0j+ gWOO Ä gWJd i9+ J0j+ gWJL i:::+ A q dWY+

YWg+ JWN 0H+ N0j+ gWNO Ä gWLL i9+ O0j+ cWNJ i1+ N0j+ OWdY i1+

O0j+ JWdL Ä JWcK i9+ J0j+ JWMg Ä JWOL i9+ J0j+ JWNJ Ä NWKJ i9+

J0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKgWL+ NYgWL+

NYYWY+ NcNWO+ NMKWc+ NOLWN+ NOLWL+ NJdWM+ NJdWJ+ NJdWN+ NJcWO+

E\FDXDU846.6DGD92,1*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E+-'jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: dOm iMdWK 9Dj

'8+⁹⁼

q ROMn i( q NWL+ >0>2_Oj+ 9? q

;

!1 ! S5#.* 132#:+ *' KLoNL+

NOc R NOgn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJK Ä gWNY

i9+ M0j+ gWNg Ä gWLK i9+ N0j+ gWLY i:::+ A q dWM+ YWJ+ LWg 0H+

N0j+ YWdM Ä YWYK i9+ J0j+ cWLJ i1+ N0j+ JWdL Ä JWcc i9+ J0j+

JWMK Ä JWJg i9+ J0j+ JWNO Ä NWKY i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL

40H+ >X>2_Oj Ñ ^??9` q NKYWK+ NYcWd+ NYNWg i:+ ^NA_>Rq JMY 0Hj+

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<

NJMWY+ NNYWd+ NNMWO+ cJWN+ OdWN+ OgWN+ JdWL+ JLWc+ A\ ib<'j

^(9^RN` q OLcg+ JKcg+ JKJc+ NgJL+ NYYY+ NYMc+ NYLg+ Ncgd+

NMdg+ NMcc+ NMOO+ NOgO+ NJdN+ NJOM+ NNgd+ NNOd+ NNNJ+

NNLL+ NLNd+ NLLN+ dcK+ gYd+ gcg+ gJO+ gLO+ cJg+ Mdd+ 0\R4-

i]-Ajo (!2(W /3'o i^4_Z!`^_jo OcgWNNLOá /37$:o OcgWNNNN+

0T6> A< >3279$ iKcm 5*8!$*o cm /R?'3?!$32+ N 96t9#$+

JgL $9j \_.Nq gWY 9#$ !$: \_.Jq dWM 9#$W

O

NcLWL i:+ A_>Rq NNWd 0Hj+ NMYWN+ NONWJ i:+ A_>Rq KWO 0Hj+

NJdWY+ NJdWL+ NJYWY+ NJNWM i:+ ^MA_>Rq OWM 0Hj+ NNcWL+ NNJWc i:+

^JA_>Rq JNWc 0Hj+ NLMWK i:+ A_>Rq JcWO 0Hj+ OgWc+ OgWN+ JgWK+

J

JLWc+ A\ ib<'j

^(9^RN` q JKMd+ NYMY+ NcKg+ NcLN+ NOgd+

<

NJgJ+ NJNL+ NNdc+ NNOg+ NLLL+ KgL+ dcJ+ YKd+ cJY+ 0\R4-

i]-Ajo (!2(W /3'o i^4_Z!`^_jo ONgWLKcMá /37$:o ONgWLKcg+

0T6>o A< >3279$ iKcm 5*8!$*o cm /R?'3?!$32+ N 96t9#$+

JgL $9j \_.Nq KWO 9#$ !$: \_.Jq NLWc 9#$W

E\FDGDEO,1C6P5RPMKLR5/6:68DVD*8FDJKLKHKGD-,-.32*5.6DM;D

:31-2,1DMD61, E+'jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2:

'8+^9:

KJm icdWK 9Dj !1 ! S5#.* 132#:+ *' Kcoc+

q Ä MMn i( q

;

E\FDXDO.6+6DGD92,1*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E+-(jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: Kdm iYKWY 9Dj

'8+⁹⁰

NWL+ >0>2Oj+ 9? q NJNRNJMn>+ N0 Z4\ iOLL 40H+ >X>2_Oj Ñ

^??9` q gWJJ R YWKd i9+ M0j+ YWgc i::+ I q dWL+ NWc 0H+ N0j+

YWgN R YWYJ i9+ J0j+ cWdK R cWdL i9+ J0j+ MWKd i1+ N0j+ JWdJ R

JWcY i9+ J0j+ JWcJ R JWJO i9+ J0j+ JWNg R NWdO i9+ J0j+

NO>Ö^N0Ü Z4\ igc 40H+ >X>2_Oj Ñ ^??9` q NKgWJ+ NYYWO+

NMKWM+ NMgWd+ NMYWN+ NMLWc+ NOLWL+ NJgWd+ NJcWY+ NJcWJ+ NJNWN+

NNYWY+ NNMWK+ NLdWc+ NLdWJ+ NLNWL+ OgWY+ OgWJ+ JdWL+ JLWc+ A\

!1 ! S5#.* 132#:+ *' dMoNY+

q RJOn i( q NWL+ >0>2_Oj+ 9? q

;

NYK R NgNn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJY Ä gWNg

i9+ c0j+ gWNg Ä gWNL i9+ J0j+ YWKY i:+ A q dWJ 0H+ N0j+ MWKK i1+

N0j+ JWgg Ä JWcc i9+ J0j+ JWMg Ä JWJK i9+ J0j+ JWNO Ä NWKJ i9+

J0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKYWK+ NYcWK+

NcLWN+ NMcWg+ NONWc+ NJdWg+ NJdWO+ NJdWL+ NJYWg+ NJMWg+ NJLWc+

<

ib<'j

^(9RN` q JKcJ+ JKJd+ JddK+ NYYM+ NYMc+ NcdL+

NcLL+ NMdM+ NOgc+ NJOM+ NNdJ+ NNOd+ NLOK+ KKY+ KJK+ gYN+

0\R4- i]-Ajo (!2(W /3'o i^4_Z!`_jo OMOWLKMYá /37$:o

OMOWLKMN+ 0T6> CX0 >3279$ idLm 5*8!$*o JLm #R

?'3?!$32+ N 96t9#$+ JgL $9j \.N q gWK 9#$ !$: \.J q NYWd

9#$W

NNKWK+ NNMWK+ OgWg+ OgWN+ JgWK+ JLWc+ A\ ib<'j

^(9^RN` q

<

NYcM+ NYOg+ NYLN+ NMKJ+ NMcJ+ NOgJ+ NJOd+ NJJO+ NJLJ+

NNgc+ NNOO+ KKc+ dJc+ gLc+ YgK+ cOc+ 0\R4- i]-Ajo (!2(W /3'o

i^4_Z!`^_joOggWLNMdtOgKWLNMdá

/37$:o

OggWLNMctOgKWLNMc+ 0T6>o CX0 >3279$ iKcm 5*8!$*o cm

/R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NNWK 9#$ !$: \_.Jq NMWK

9#$W

E\FDWDI,-26:*DGDEHD+,-26:*92,1*8FDJKLKHKGD-,-.32*5.6DM;D

:31-2,1DMD61, E+(jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2:

'8+^9:

E\FDGDEHDI,-26:*DLKVD5/+,-2*892,1*8FDJKLKHKGD-,-.32*5.6D

M;D:31-2,1DMD61, E+.j+ 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2:

'8+^9:

Kgm iYcWO 9Dj !1 ! S5#.* 132#:+ *' KYoM+

q _OMn i( q NWL+

;

>0>2_Oj+ 9? q NMK R NMgn>+ ^N0 Z4\ iOLL 40H+ >X>2_Oj Ñ ^??9`

q gWNK R gWLK i9+ J0j+ gWLN i:+ A q KWL 0H+ N0j+ YWgN i::+ A q

KWL+ OWL 0H+ N0j+ YWdL R YWgM i9+ J0j+ YWcg i:+ A q OWL 0H+ N0j+

MWKd i1+ N0j+ OWYK i1+ O0j+ OWgO i1+ O0j+ JWYY i:+ A q MWc 0H+ J0j+

JWgd R JWcc i9+ J0j+ JWMK R JWJc i9+ J0j+ JWNg R NWdc i9+ J0j+

^NO>Ö^N0Ü Z4\ igc 40H+ >X>2_Oj Ñ ^??9` q NKgWJ+ NYYWO+ NcdWJ+

NcYWg+ NMOWd+ NOdWg+ NJKWL+ NJYWY+ NNgWM+ NNMWM+ NNOWK+ NNOWd+

Kgm iYMWK 9Dj !1 ! S5#.* 132#:+ *' Kcoc+

q R cJn i(q NWL+

;

>0>2_Oj+ 9? q YN R YOn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q

gWJJ R YWKc i9+ M0j+ YWdO i1+ J0j+ MWKO i1+ N0j+ OWYO i1+ O0j+

JWgK R JWYL i9+ J0j+ JWMY R JWON i9+ J0j+ JWNK i1+ Y0j+ NWKd R

JWNL i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q

NKgWJ+ NYYWO+ NccWc+ NMKWc+ NMNWc+ NOLWY+ NOLWN+ NJdWJ+ NJgWY+

NJcWK+ NJcWN+ NNYWY+ NNcWL+ cKWY+ OgWO+ OgWJ+ JdWN+ JLWc+ NYWM+

NLMWK+ ccWg+ ccWO+ OgWc+ OgWJ+ JdWL+ JLWY+ A\ ib<'j

^(9^RN` q

<

JKcM+ JKMY+ NYcK+ NYOK+ NcNN+ NMKY+ NOgg+ NJcY+ NJJJ+

NNKg+ NLJd+ KKd+ dOJ+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo

OcKWNJcKá /37$:o OcKWNJcM+ 0T6>o CX0 >3279$ iKcm

5*8!$*o cm /R?'3?!$32+ N 96t9#$+ JgM $9j \_.Nq NdWL 9#$

!$: \_.Jq JOWM 9#$W

A\ ib<'j

^(9^RN` q OLJd+ JKMd+ JdKg+ JdgL+ JdJM+ NYYJ+

<

NYMM+ NcdN+ NMdc+NMcY+ NOgc+ NJOc+ NJJc+ NNdN+ NNJg+

NLNY+ KKc+ KNN+ gcg+ gOJ+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo

OcgWNMYgá /37$:o OcgWNMYN+ 0T6> CX0 >3279$ iKcm

5*8!$*o cm /R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NLWJ 9#$

!$: \_.Jq NJWN 9#$W

E\FDXDI,-2*8DGD92,1*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E+-,jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: gKm iMcWK 9Dj

'8+⁹⁰

E\FDWDO.6+6DGDEHD+,-26:*92,1*8FDJKLKHKGD-,-.32*5.6DM;D

:31-2,1DMD61, E+/jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2:

'8+^9:

!1 ! S5#.* 132#:+ *' Kcoc+

q ROMn i( q NWL+ >0>2_Oj+ 9? q

;

NYK R NgNn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJM Ä gWNd

i9+ M0j+ gWNY Ä gWLY i9+ N0j+ YWKd i:+ A q gWd 0H+ N0j+ YWKL i1+

N0j+ YWdM i:+ A q gWd 0H+ N0j+ cWLJ i1+ N0j+ JWgd Ä JWcd i9+ J0j+

JWMg Ä JWOO i9+ J0j+ JWOL i1+ O0j+ JWNO Ä NWKO i9+ J0j+ ^NO>Ö^N0Ü

Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKgWN+ NYYWM+ NMKWM+ NMYWc+

NOgWd+ NJKWd+ NJdWc+ NJdWL+ NJYWM+ NJYWN+ NJJWc+ NNYWK+ NNcWL+

dKm iYdWY 9Dj !1 ! S5#.* 132#:+ *' KgoO+

q _dJn i( q NWL+

;

>0>2_Oj+ 9? q NdJ R NdMn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9`

q gWJY i::+ A q JWc+ KWL 0H+ N0j+ gWJN i:+ A q JWc 0H+ N0j+ gWNK R

gWLc i9+ J0j+ YWKc i:+ A q KWL 0H+ N0j+ YWdJ R YWYd i9+ J0j+ MWKc

i1+ N0j+ OWgM i1+ O0j+ JWdM R JWcL i9+ J0j+ JWMd R JWJL i9+ J0j+

JWNO RNWdO i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9`

q NKYWK+ NYcWd+ NcdWM+ NMdWY+ NOdWN+ NOJWd+ NOLWg+ NJKWL+

OgWg+ OgWJ+ JdWN+ JNWJ+ JLWc+ A\ ib<'j

^(9^RN` q NYYN+ NYMO+

<

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The Journal of Organic Chemistry

NJdWL+ NNdWM+ NNgWc+ NNMWd+ NNMWN+ ccWO+ OgWN+ OgWN+ JgWK+ JLWc+ NJYWO+ NNgWM+ NNMWJ+ NNMWL+ NNOWK+ ccWg+ OdWM+ OgWN+ JdWN+ JLWc+

A\ ib<'j

^(9^RN` q JKMd+ JKOM+ JdKL+ JdgY+ JdOM+ NYYO+

A\ ib<'j

^(9^RN` q OLYN+ OLOJ+ OLNO+ JKcY+ JKMc+ JKJY+

1

2

3

4

<

NYMc+ NYNN+ NcLK+ NOgc+ NJcY+ NJOg+ NNgY+ NNJK+ NLJg+ KKg+

dON+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_joMLgWLJcKá /37$:o

MLgWLJcO+ 0T6> CX0 >3279$ iKcm 5*8!$*o cm /R?'3?!$32+

N 96t9#$+ JgL $9j \_.Nq NMWg 9#$ !$: \_.Jq JLWY 9#$W

NYcK+ NYOK+ Ncdg+ NMKN+ NOgM+ NJNY+ NNKg+ KKg+ dOc+ dJO+

gLJ+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo OJKWNNcMá /37$:o

OJKWNNMd+ 0T6> CX0 >3279$ iKcm 5*8!$*o cm /R?'3?!$32+

N 96t9#$+ JgM $9j \_.Nq NOWc !$: \_.Jq NcWN 9#$W

5

6

7

8

9

E\FDGDT2,1*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E+0,jW

E\FDWDE.*'.DO4-*8FDGDEHD+,-26:*92,1*8FDJKLKHKGD-,-.32*5.6D

M;D:31-2,1DMD61, E+%jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2:

'8+^9:

q _gMn i( q NWL+

;

0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: KMm icJWL 9Dj !1 !

'8+^9:

S5#.* 132#:+ *'o Kcoc+

q ÄYdn i( q NWL+ >0>2_Oj+ 9? q NOL

Kgm igLWO 9Dj !1 ! S5#.* 132#:+ *' KYoM+

;

R NONn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJc Ä YWKK i9+

K0j+ cWLg i1+ N0j+ JWgK Ä JWcd i9+ J0j+ JWMY Ä JWJK i9+ J0j+

JWNN Ä NWKM i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9`

q NKgWN+ NYYWM+ NMKWY+ NMYWO+ NOLWJ+ NJdWc+ NJdWL+ NJgWg+

NJYWc+ NJcWY+ NJcWJ+ NNYWY+ NNMWK+ OgWK+ OgWN+ JdWL+ JLWc+ A\

>0>2_Oj+ 9? q NNK R NJJn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9`

q gWJL i::+ A q dWc+ JWc 0H+ N0j+ gWNY R gWNN i9+ J0j+ gWLK i:+ A

q JWc 0H+ N0j+ gWLN i:+ A q dWc 0H+ N0j+ YWdL R YWgL i9+ J0j+

cWLJ i1+ N0j+ OWgM i1+ O0j+ JWgd R JWcO i9+ J0j+ JWMK R JWJO i9+

J0j+ JWNO R NWdM i9+ J0j+ NWJO i1+ K0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+

>X>2_Oj Ñ ^??9` q NKgWJ+ NYYWc+ NcdWL+ NMdWJ+ NMgWg+ NOdWd+

NJdWK+ NJYWY+ NJcWL+ NJMWd+ NNYWL+ NNcWO+ NNOWd+ ccWO+ OgWJ+

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

25

26

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

<

ib<'j

^(9^RN` q OLcK+ OLJc+ JKcM+ JddK+ JdYK+ NYYJ+

NYMM+ NMdY+ NMcc+ NOgM+ NJOg+ NJJY+ NNgg+ NNOL+ KKY+ gcK+

0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo JKKWNLMdá /37$:o

JKKWNLMO+ 0T6> CX0 >3279$ iKcm 5*8!$*o cm /R?'3?!$32+

N 96t9#$+ JgM $9j \_.NqNNWL 9#$ !$: \_.Jq NOWM 9#$W

<

OgWJ+ OMWc+ ONWc+ JdWN+ JLWY+ A\ ib<'j

^(9^RN` q JKYL+ JKLO+

JdYK+ JdON+ NYYL+ NYMN+ Ncdg+ NcLK+ NMKd+ NOgY+ NJcY+

NNgc+ NNOJ+ NLOM+ KKg+ dJd+ 0\R4- i]-Ajo (!2(W /3'o

i^4_Z!`^_joOdcWNgdLá /37$:o OdcWNggM+ 0T6> CX0 >3279$

iKcm 5*8!$*o cm /R?'3?!$32+ N 96t9#$+ JJL $9j \_.Nq dWg

9#$ !$: \_.Jq NLWc 9#$W

E\FDWDU846.6DGD92,1*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E+0'jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: dLm iMgWN 9Dj

'8+⁹⁼

!1 ! S5#.* 132#:+ *'o KOog+

q ÄYdn i( q NWL+ >0>2_Oj+ 9? q

;

NYg R NYKn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJg Ä gWNK

i9+ M0j+ gWNg Ä gWNJ i9+ N0j+ gWLc i::+ A q KWL+ MWg 0H+ N0j+

YWdg i:::+ A q dWK+ gWd+ OWL 0H+ N0j+ YWgK i:::+ A q dWY+ OWL+ LWg

0H+ N0j+ cWLJ i1+ N0j+ JWgK Ä JWcg i9+ J0j+ JWMg Ä JWJK i9+ J0j+

JWNN Ä NWKJ i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9`

q NKYWK+ NYYWO+ NcKWc i:+ ^NA_>Rq JMOWc 0Hj+ NMcWg+ NMcWY i:+ ^MA_>R

E\FDGDEJD!-2*892,1*8FDJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E+)jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: Kdm icKWg 9Dj !1

'8+^9:

! S5#.* 132#:+ *' KYoM+

q Ä gdn i( q NWL+ >0>2_Oj+ 9? q NOOR

;

NOMn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJJ R YWKL i9+

d0j+ cWOO i1+ N0j+ OWNY i[:+ A q gWc+ MWJ 0H+ J0j+ JWdO R JWcd i9+

J0j+ JWMc R JWOL i9+ J0j+ JWNY R NWKc i9+ J0j+ NWMN i.+ A q gWc

0H+ O0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKgWN+

NYYWO+ NMKWJ+ NMMWg+ NMLWK+ NJKWK+ NJKWJ+ NJdWc+ NJgWc+

NJYWMM+ NJYWOK+ NJYWJK+ NJcWN+ NNYWg+ NNcWY+ OgWJ+ OOWM+ JdWN+

q JWM 0Hj+ NJdWg+ NJdWL+ NJgWN i:+ ^OA_>Rq gWg 0Hj+ NJYWd+ NNdWL

O

J

i:+ A_>Rq dWY 0Hj+ NNYWN i:+ A_>Rq JOWL 0Hj+ NNMWd i:+ A_>R

q

M

JOWd 0Hj+ NNMWL+ OdWO i:+ A_>Rq NWO 0Hj+ OgWN+ JdWL+ JLWc+ A\

ib<'j

^(9^RN` q JKYg+ JdKL+ NYYM+ NYMc+ Ncdd+ NMdY+

JcWc+ JLWY+ NcWc+ A\ ib<'j

^(9^RN` q JKYO+ JKJd+ JdKJ+

<

NMcc+ NJcg+ NJNc+ NNKc+ NNOc+ NLKd+ KKK+ KNd+ dgd+ dOM+

dLc+ gON+ gLK+ YJJ+ cOL+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo

ONgWLKcMá /37$:o ONgWLKcM+ 0T6> A< >3279$ iKcm 5*8!$*o

cm /R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq KWJ 9#$ !$:

\_.Jq NLWK 9#$W

Jdgd+ JdMg+ NYMM+ NcdL+ NMdc+ NOgO+ NJOM+ NNgg+ NNOJ+ KKM+

gYJ+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo OJgWNOYNá /37$:o

OJgWNOcY+ 0T6> CX0 >3279$ iKcm 5*8!$*o cm /R?'3?!$32+

N 96t9#$+ JML $9j \_.Nq dWL 9#$ !$: \_.Jq KWd 9#$W

E\FDGDE9DS68*8,-2*1*8FDJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E+1jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: Kdm iYNWY 9Dj !1

'8+^9>

E\FDWDI,-2*8DGD92,1*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E+0(jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: dOm iMdWJ 9Dj

'8+^9:

! S5#.* 132#:+ *' dKoNN+

q _NJn i( q NWLL+ >0>2_Oj+ 9? q

;

Mg R MKn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWMY i::+ A q

gWg+ NWg 0H+ N0j+ gWJg Ä gWJL i9+ O0j+ gWNK Ä gWNJ i9+ N0j+ gWLY

Ä YWKK i9+ O0j+ cWLJ i1+ N0j+ JWgL i:.+ A q NgWY+ cWM 0H+ N0j+

JWYM Ä JWcJ i9+ J0j+ JWMK Ä JWOg i9+ N0j+ JWJK i1+ O0j+ JWNK Ä

JWLN i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q

NKYWY+ NYYWg+ NMKWL+ NOgWK+ NONWd+ NOLWJ+ NJdWK+ NJdWc+ NJcWO+

NJNWK+ NJLWM+ NNYWd+ NNNWO+ KLWc+ dLWY+ OgWL+ JdWL+ JMWc+ JNWc+

!1 ! S5#.* 132#:+ *'o dKoNN+

q ÄJYn i( q LWc+ >0>2_Oj+ 9? q

;

NOL R NONn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJc Ä gWNK

i9+ M0j+ gWNY Ä gWLK i9+ N0j+ YWKK Ä YWKM i9+ J0j+ YWdK i1+

N0j+ cWLN i1+ N0j+ JWgg Ä JWcg i9+ J0j+ JWMc Ä JWJd i9+ J0j+

JWJN i1+ O0j+ JWNN Ä NWKJ i9+ J0jW ^NO>Ö^N0Ü Z4\ iNLL 40H+

>X>2_Oj Ñ ^??9` q NKgWN+ NYYWM+ NMgWY+ NMYWc+ NOMWg+ NOLWO+

NJdWc+ NJdWM+ NJdWN+ NJYWM+ NJcWN+ NNYWO+ NNMWd+ OdWL+ OgWJ+

^(9^RN` q NYOd+ NcLO+ NMKN+

JLWc+ A\ ib<'j

^(9^RN` q OMMc+ NYYY+ NYMg+ NcdO+ NcLK+

<

JdWN+ JLWK+ JLWY+ A\ ib<'j

NMcM+ NOgc+ NJMM+ NJNM+ NNgY+ NNOg+ NLLK+ KKN+ gOd+ gJM+

gLN+ 0\R4- i]-Ajo (!2(W /3'o i^4_0`^_jo JKNWNOdLá /37$:o

JKNWNOdN+ 0T6> CX0 >3279$ iKcm 5*8!$*o cm /R?'3?!$32+

N 96t9#$+ JgL $9j \_.NqdWJ 9#$ !$: \_.Jq KWM 9#$W

NMdK+ NMcc+ NOgJ+ NJMK+ NJOO+ NNgO+ NNOJ+ KKg+ dNd+ gcd+

cJK+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo OOgWNJLcá /37$:o

OOgWNJJL+ 0T6> AA >3279$ iKcm 5*8!$*o cm /R?'3?!$32+ N

96t9#$+ JcL $9j \_.Nq NJWg 9#$ !$: \_.Jq NYWd 9#$W

E\FDWDI,-26:*DGD92,1*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD

61, E+0-jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: KOm icgWL

'8+^9:

E\FDGDY)6>4-*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E+2jW

0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: KKm icLWd 9Dj !1 !

'8+⁹⁰

q Ä NJdn i( q LWc+ >0>2_Oj+

;

9Dj !1 ! S5#.* 132#:+ *' KdoJ+

q Ä NOJn i( q NWL+ >0>2_Oj+

P*223S#15 132#:+ *' KNWcodWc+

;

9? q NLJRNLcn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJM

R gWNg i9+ M0j+ gWNY R gWLY i9+ N0j+ gWLJ i:+ A q KWL 0H+ N0j+

YWgJ i::+ A q KWL+ OWL 0H+ N0j+ YWcK i:+ A q OWL 0H+ N0j+ cWLJ i1+

N0j+ OWYK i1+ O0j+ JWgK R JWcL i9+ J0j+ JWMK R JWJL i9+ J0j+

JWNN R NWdO i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9`

q NKgWN+ NYYWc+ NcYWg+ NMYWJ+ NMOWd+ NJdWc+ NJdWL+ NJYWc+

9? q gK R dNn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJJ Ä

gWNM i9+ J0j+ gWNM Ä gWLY i9+ N0j+ gWLJ i::+ A q dWL+ NWO 0H+

N0j+ OWKO i.+ A q YWc 0H+ N0j+ JWYc i:.+ A q NgWg+ cWL 0H+ N0j+

JWYL Ä JWMY i9+ J0j+ JWMJ Ä JWJd i9+ N0j+ JWNO Ä NWKY i9+ J0j+

NWYN Ä NWMc i9+ N0j+ NWML Ä NWOJ i9+ J0j+ LWKO i:+ A q YWY 0H+

O0j+ LWdM i:+ A q YWc 0H+ O0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj

ACS Paragon Plus Environment

The Journal of Organic Chemistry

Page 16 of 26

Ñ ^??9` q NKgWc+ NYgWY+ NcLWg+ NJKWO+ NJgWO+ NJYWK+ NJMWY+

NNYWM+ NNYWL+ MdWN+ OgWO+ JKWg+ JdWN+ JMWd+ JOWd+ JJWM+ JLWg+ A\

i^4_Z!`^_jo ONOWNNKKá /37$:o ONOWNJLN+ 0T6> CX0 >3279$

iKcm 5*8!$*o cm /R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq gWg

9#$ !$: \_.Jq dWK 9#$W

1

2

ib<'j

^(9^RN` q NYcK+ NYMM+ Ncgd+ NMdO+ NMcY+ NOdM+

<

3

4

5

6

7

8

9

NOYd+ NJML+ NJJN+ NNdN+ NNOJ+ NNJJ+ KKM+ gcg+ 0\R4- i]-Ajo

(!2(W /3'o i^4_Z!`^_jo JgKWNOYNá /37$:o JgKWNOdY+ 0T6> CX0

>3279$ iKdm 5*8!$*o Jm /R?'3?!$32+ N 96t9#$+ JgL $9j

\_.Nq dWd 9#$ !$: \_.Jq NgWY 9#$W

E-FDXK[D&/+,-2*8DGD92,1*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD

61, E+6jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: dOm icLWc

'8+⁹⁰

9Dj !1 ! S5#.* 132#:+ *' dcoNc+

q Ä Kn i( q NWY+ >0>2_Oj+

;

9? q NcN R NcOn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJM

Ä gWNc i9+ M0j+ gWNO Ä gWLc i9+ N0j+ YWdJ i1+ N0j+ YWgM i1+ N0j+

cWLK i1+ N0j+ JWgN Ä JWcN i9+ J0j+ JWMM Ä JWON i9+ J0j+ JWOL i1+

O0j+ JWLd i1+ O0j+ JWLc Ä NWdc i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL

40H+ >X>2_Oj Ñ ^??9` q NKgWN+ NYYWJ+ NcLWM+ NMcWL+ NOgWd+

NOgWY+ NJdWd+ NJdWO+ NJgWd+ NJYWJ+ NJNWN+ NNYWN NNMWY+ OgWN+

E\FDGDZ/1*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E+3jW

0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: Ydm iOLWd 9Dj !1 !

'8+⁹⁰

(323'2*11 2#[7#:+ *' ddoNJ+

q Ä Ycn i( q LWMO+ >0>2_Oj+ ^N0

;

Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWJM Ä gWNY i9+ J0j+ gWNM

Ä gWLd i9+ N0j+ gWLJ i:+ A q dWN 0H+ N0j+ cWdg i:::+ A q NYWd+

NLWL+ YWc 0H+ N0j+ MWKg i:+ A q NLWL 0H+ N0j+ MWdK i:+ A q NgWL

0H+ N0j+ MWcO i:+ A q YWM 0H+ N0j+ JWgJ Ä JWMg i9+ O0j+ JWMc Ä

JWOO i9+ N0j+ JWNc Ä JWLL i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+

>X>2_Oj Ñ ^??9` q NKgWO+ NYgWN+ NMKWK+ NMLWY+ NOLWL+ NJgWK+

NJMWK+ NJOWg+ NNYWc+ NNMWJ+ NNOWL+ OgWJ+ OcWY+ JdWN+ JLWg+ A\

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<

OcWO+ JdWL+ JNWN+ JLWM+ NKWL+ A\ ib<'j

^(9^RN` q NYcK+ NYMM+

Ncgc+ NMKL+ NMcJ+ NOdL+ NOYd+ NONL+ NJdc+ NJMM+ NJOL+

NJNK+ NNdY+ NNJK+ NLOL+ NLLY+ dMO+ gNK+ YKd+ 0\R4- i]-Ajo

(!2(W /3'o i^4_Z!`^_jo OLcWNcOYá /37$:o OLcWNcOK+ 0T6> AA

>3279$ iKdm 5*8!$*o Jm /R?'3?!$32+ N 96t9#$+ JgL $9j

\_.Nq KWM 9#$ !$: \_.Jq NNWY 9#$W

<

i/#29j

^(9^RN` q NYYJ+ NYMM+ NcdL+ NMdY+ NMMc+ NOgY+

NJOY+ NNdL+ NNOM+ KKO+ KNc+ gcY+ 0\R4- i]-Ajo (!2(W /3'o

i^4_0`^_jo JMKWLddYá /37$:o JMKWLddg+ 0T6> AA >3279$

iKdm 5*8!$*o Jm /R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NLWN

9#$ !$: \_.Jq NNWd 9#$W

E\FDM\DEHDI,-26:*92,1*8FDXKWK[KM\D-,-.32*5.6DG;D

PMKLR5/6:686PHKVD>R:31-2,1DGD61, E7+jW 0*8!$*t4;<] iKoNj

'8+⁹⁰

!1 *27*$.+ h#*2: dLm icNWO 9Dj !1 ! S5#.* 132#:+ *' KMoY+

;

q _JLn i( q LWcL+ >0>2_Oj+ 9? q cJ R cMn>+ ^N0 Z4\ iOLL 40H+

>X>2_Oj Ñ ^??9` q gWNd Ä gWLd i9+ J0j+ YWdM Ä YWgN i9+ J0j+

YWcd i1+ N0j+ YWMg i1+ N0j+ cWKN i:+ A q NWO 0H+ N0j+ cWdg i:+ A q

NWO 0H+ N0j+ MWdd i1+ N0j+ OWgM i1+ O0j+ JWgY Ä JWcO i9+ J0j+

JWMY Ä JWJM i9+ J0j+ JWNO Ä NWKL i9+ J0j+ ^NO>Ö^N0Ü Z4\ iNLL

40H+ >X>2_Oj Ñ ^??9` q NKgWJ+ NYYWL+ NcdWJ+ NMYWd+ NMMWd+

NMMWL+ NOdWd+ NJdWK+ NNgWK+ NNMWM+ NNOWK+ NLdWM+ NLNWY+ KdWJ+

E\FDGD!-2*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E+4jW

0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: Kgm iMMWO 9Dj !1 !

'8+⁹⁰

N

(323'2*11 2#[7#:+ *' KNoK+

q Ä NNJn i( q LWc+ >0>2_Oj+ 0

;

Z4\ iMLL 40H+ >523'3/3'9R5j Ñ ^??9` q gWJN Ä gWNM i9+

J0j+ gWNO Ä gWLg i9+ N0j+ YWKK i:+ A q dWJ 0H+ N0j+ OWKc i.+ A q

MWK 0H+ N0j+ JWYY i:.+ A q NgWY+ cWL 0H+ N0j+ JWYN Ä JWMg i9+

J0j+ JWMJ Ä JWOJ i9+ N0j+ JWNJ Ä NWKK i9+ J0j+ NWgY Ä NWcY i9+

J0j+ LWYg i.+ A q gWc 0H+ O0j+ ^NO>Ö^N0Ü Z4\ iNLN 40H+ >X>2_Oj

Ñ ^??9` q NKgWd+ NYdWL+ NcLWd+ NJKWN+ NJgWO+ NJcWY+ NJMWd+

^(9^RN` q NYcL+ NYNd+

<

ccWO+ OgWO+ OgWN+ JgWK+ JLWc+ A\ ib<'j

NcLK+ NMdJ+ NOdO+ NJcc+ NJMN+ NJNc+ NNdO+ NNMJ+ NLOc+ KKd+

KOY+ cOJ+ 0\R4- i]-Ajo (!2(W /3'o i^4_0`^_jo OgOWNLMYá /37$:o

OgOWNLMJ+ 0T6> CX0 >3279$ iKLm 5*8!$*o NLm /R

?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NdWK 9#$ !$: \_.Jq JJWK

9#$W

<

NNYWN+ NNOWd+ OgWO+ OJWM+ OLWN+ JdWL+ JLWd+ KWO+ A\ ib<'j

^(9^RN` q NYYL+ NYMM+ NcdN+ NMdY+ NMcc+ NOdg+ NJOc+ NNdM+

NNOc+ KKN+ gcY+ 0\R4- i]-Ajo (!2(W /3'o i^4_0`^_jo JcNWNLMOá

/37$:o JcNWNLMO+ 0T6> CX0 >3279$ iKdm 5*8!$*o Jm /R

?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NLWN 9#$ !$: \_.Jq NNWd

9#$W

a@(..;!+(5- !913,-:6: 08 *8/ $.-26R5P:'38P "*$HP2

!2(3532 &8 iNWJM D+ MWLL 9932+ NWL *[7#FWj+ N+OR

(P(235*8!$*:#3$* '( iLWYgO D+ YWLL 9932+ NWc *[7#FWj !$:

(!.!2P1. E idLWO 9D+ LWNJL 9932+ O 932 mj S*'* :#1132F*:

#$ (523'3/3'9 iJL 96j !. \;W ;5* '*!(.#3$ 9#8.7'* S!1

1.#''*: /3' N :!P 7$.#2 (39?2*.* (3$179?.#3$ 3/ .5* 1.!'.#$D

9!.*'#!2W ;5*$ 9D.327*$*172/3$#( !(#: 93$35P:'!.* iLWNcJ

D+ LWdLL 9932+ JL 932mj S!1 !::*: !$: .5* '*!(.#3$

9#8.7'* S!1 /7'.5*' 1.#''*: /3' M 5 !. MLn>W ;5* ('7:*

'*!(.#3$ 9#8.7'* S!1 ?7'#/#*: "P 153'. /2!15

(5'39!.3D'!?5P i5*8!$*t4;<] KoNj .3 !//3': .5* :*1#'*:

8!$.5*$3$* *8 iNWOg D+ OWcY 9932+ dK m+ *' KgoOjW

E\FDXDE.*'.DO4-*8FDGD92,1*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1D

MD61, E+5jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: KNm iYLWc

N

9Dj !1 ! S5#.* 132#:+ *' cLocL+ 9? q NYK R NgNn>+ 0 Z4\

iOLL 40H+ >X>2_Oj Ñ ^??9` q gWJc Ä gWNd i9+ M0j+ gWNY Ä gWLg

i9+ J0j+ gWLY Ä gWLL i9+ J0j+ cWLO i1+ N0j+ JWgK Ä JWcg i9+

J0j+ JWMg Ä JWJd i9+ J0j+ JWNN Ä NWKN i9+ J0j+ NWJK i1+ K0j+

^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKgWN+ NYYWY+

NcNWM+ NMKWJ+ NMYWM+ NJKWY+ NJdWc+ NJdWL+ NJYWM+ NJJWc+ NJJWM+

<

NNcWL+ NNOWM+ OgWg+ OgWJ+ OMWg+ ONWM+ JdWN+ JLWY+ A\ ib<'j

^(9^RN` q NYMM+ NOgY+ NJYK+ NJJc+ NNdL+ NNOY+ KKg+ gLLW cJd+

0\R4- i]-Ajo (!2(W /3'o i^4_b`^_jo OgNWNMNOá /37$:o

OgNWNOKNW

%*$*'!2 T'3(*:7'* /3' ]$!$.#31*2*(.#F* A::#.#3$ 3/ O+cR

TP'!$:#3$*W

$.-26R5P:'38P "*$HP2 !2(3532 & iLWN 9932+ NWL *[7#FWj+ O+cR

?P'!$:#3$* 'F iNgWN 9D+ LWNc 9932+ NWc *[7#FWj !$: (!.!2P1.

E iOWM 9D+ LWLLc 9932+ c 932 mj S*'* :#1132F*: #$

(523'3/3'9 iLWd 96j !. Ln>W ;5* '*!(.#3$ 9#8.7'* S!1

1.#''*: /3' N :!P !. Ln> 7$.#2 (39?2*.* (3$179?.#3$ 3/ .5*

1.!'.#$D 9!.*'#!2 !$: .5*$ N :!P !. \;W ;5* ('7:* '*!(.#3$

9#8.7'* S!1 ?7'#/#*: "P 153'. /2!15 (5'39!.3D'!?5P

i5*8!$*t4;<] KoNj .3 !//3': .5* :*1#'*: 38!8!$.5*$3$*1W

;5* *$!$.#39*'#( '!.#31 S*'* :*.*'9#$*: "P 0T6> 3$ !

(5#'!2 1.!.#3$!'P ?5!1*W

E\FDVDI,-2*8DGD92,1*8DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E+&jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: gMm iMOWL 9Dj !1

! S5#.* 132#:+ *' cgoMO+ 9? q NcK R NYNn>+ ^N0 Z4\ iMLL 40H+

>X>2_Oj Ñ ^??9` q gWJM Ä gWNd i9+ M0j+ gWNc Ä gWLd i9+ N0j+

gWLc Ä YWKK i9+ N0j+ YWKg Ä YWdK i9+ J0j+ cWLd Ä cWLJ i9+ N0j+

JWdJ Ä JWcg i9+ J0j+ JWMg Ä JWOg i9+ J0j+ JWOc i1+ O0j+ JWNN Ä

NWKY i9+ J0j+ ^NO>Ö^N0Ü Z4\ igc 40H+ >X>2_Oj Ñ ^??9` q NKgWN+

NYYWO+ NMdWL+ NMYWM+ NJKWN+ NJdWc+ NJdWL+ NJgWg+ NJYWM+ NJcWd+

<

NJcWJ+ NJMWY+ NNcWL+ OdWN+ OgWJ+ JdWN+ JLWY+ NYWL+ A\ ib<'j

^(9^RN` q NYYL+ NYMY+ NcdK+ NMYd+ NMcc+ NOgM+ NJYc+ NJNK+

NNdO+ NNJg+ NLgM+ gYc+ gMg+ gOJ+ YKd+ 0\R4- i]-Ajo (!2(W /3'o

E\FDGDT2,1*8DLD6:6DJKLKHKGD-,-.32*5.6DM;D:31-2,1DMD61,

E8,jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: KMm iJYWJ 9Dj !1

ACS Paragon Plus Environment

Page 17 of 26

The Journal of Organic Chemistry

YWdM i1+ J0j+ MWKY i1+ N0j+ MWYO i:+ A q NYWO 0H+ N0j+ MWMK i:.+ A

q ÄYdn i( q LWc+ >0>2_Oj+ 9? q

'8+⁹⁰

! S5#.* 132#:+ *' KNWcodWc+

;

NJL R NJJn>+ ^N0 Z4\ iOLL 40H+ >X>2_Oj Ñ ^??9` q gWJK Ä gWLJ

i9+ K0j+ cWLK i1+ N0j+ MWYN i:+ A q NYWO 0H+ N0j+ MWMK i:.+ A q

NYWO+ NWc 0H+ N0j+ MWNK i:+ A q NYWJ 0H+ N0j+ MWLg i::+ A q NYWN+

NWg 0H+ N0j+ ^NO>Ö^N0Ü Z4\ igc 40H+ >X>2_Oj Ñ ^??9` q NKJWK+

NYOWc+ NMKWN+ NMcWN+ NOLWY+ NJdWg+ NJdWJ+ NJdWN+ NJYWK+ NJcWd+

1

2

3

4

5

6

q NYWO+ NWc 0H+ N0j+ MWJN i:+ A q NYWJ 0H+ N0j+ MWLY i::+ A q NYWN+

NWd 0H+ N0j+ OWYc i1+ O0j+ JWJL i1+ Y0j+ ^NO>Ö^N0Ü Z4\ iNLL

40H+ >X>2_Oj Ñ ^??9` q NKOWL+ NYOWM+ NccWd+ NMKWL+ NMLWO+

NOLWK+ NOLWc+ NJdWM+ NJdWL+ NJcWg+ NJcWM+ NNYWd+ NNJWd+ gNWK+

<

YMWg+ cKWg+ OYWN+ NYWO+ A\ ib<'j

^(9^RN` q OMMO+ NYcd+

^(9^RN` q

NYMY+ NMdM+ NOKN+ NJcJ+ NJML+ NNgJ+ NNOJ+ gcY+ 0\R4-

i]-Ajo (!2(W /3'o i^4_Z!`^_jo OcKWNJcMá /37$:o OcKWNJcM+

0T6> CX0 >3279$ iKcm 5*8!$*o cm /R?'3?!$32+ N 96t9#$+

JgL $9j \_.Nq NNWg 9#$ !$: \_.Jq NJWK 9#$W

<

NJcWL+ NNYWd+ NNJWY+ gNWK+ YMWg+ OYWg+ A\ ib<'j

NYgY+ NYcY+ NMdc+ NOKN+ NOcO+ NJMJ+ NNgO+ NNJM+ gYO+ gNL+

0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo OLNWLdOcá /37$:o

OLNWLdOc+ 0T6> CX0 >3279$ iKcm 5*8!$*o cm /R?'3?!$32+

N 96t9#$+ JgL $9j \_.Nq NOWM 9#$ !$: \_.Jq NgWL 9#$W

7

8

9

E\FDWDE.*'.DO4-*8FDGDEHD+,-26:*92,1*8FDLD6:6DJKLKHKGD

-,-.32*5.6DM;D:31-2,1DMD61, E8/jW 0*8!$*t4;<] iKoNj !1

*27*$.+ h#*2: KNm iOOWJ 9Dj !1 ! P*223S 132#:+ *' KJWcogWc+

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E\FDGDEHDI,-26:*92,1*8FDLD6:6DJKLKHKGD-,-.32*5.6DM;D

:31-2,1DMD61, E8'jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2:

'8+⁹⁰

'8+⁹_;⁰

N

q cgn i( q LWc+ >0>2_Oj+ 9? q OM R OYn>+ 0 Z4\ iOLL

40H+ >X>2_Oj Ñ ^??9` q gWJO i::+ A q dWY+ JWM 0H+ N0j+ gWNd Ä

gWNJ i9+ J0j+ gWNL i:+ A q JWO 0H+ N0j+ gWLJ i:+ A q dWY 0H+ N0j+

YWdO Ä YWgO i9+ J0j+ cWLM i1+ N0j+ MWcd i:+ A q NYWO 0H+ N0j+

MWMc i:.+ A q NYWO+ NWM 0H+ N0j+ MWNd i:+ A q NYWN 0H+ N0j+ MWLM

i::+ A q NYWN+ NWd 0H+ N0j+ OWgc i1+ O0j+ NWJO i1+ K0j+ ^NO>Ö^N0Ü

Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKOWN+ NYOWc+ NcdWO+ NMdWK+

NMgWJ+ NOgWY+ NJKWN+ NJgWN+ NJcWJ+ NJMWc+ NNYWJ+ NNMWL+ NNJWK+

ddm iJgWN 9Dj !1 ! P*223S 132#:+ *' KJod+

q ÄOdn i( q

;

N

LWc+ >0>2_Oj+ 9? q Oc R Ogn>+ 0 Z4\ iMLL 40H+ >X>2_Oj Ñ

^??9` q gWJO Ä gWLc i9+ Y0j+ YWdJ Ä YWgc i9+ J0j+ cWLM i1+ N0j+

MWcK i:+ A q NYWO 0H+ N0j+ MWMK i:.+ A q NYWO+ NWc 0H+ N0j+ MWNd

i:+ A q NYWN 0H+ N0j+ MWLY i::+ A q NYWN+ NWd 0H+ N0j+ OWgM i1+

O0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKOWL+ NYOWO+

NcdWM+ NMKWN+ NOgWY+ NOLWY+ NJKWJ+ NJdWL+ NJcWd+ NJcWO+ NNYWd+

^(9^RN` q

<

NNMWN+ NNJWd+ gNWK+ YMWY+ ccWO+ OcWK+ A\ ib<'j

gNWK+ YMWg+ ccWO+ OYWN+ OMWY+ ONWc+ A\ ib<'j

^(9^RN` q OMOM+

<

OMMJ+ NYgO+ NYcJ+ NcLK+ NOKM+ NJcc+ NJMN+ NNgO+ NLOJ+ gcY+

0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo OONWLKMNá /37$:o

OONWLKMJ+ 0T6> CX0 >3279$ iKcm 5*8!$*o cm /R?'3?!$32+

N 96t9#$+ JgL $9j \_.Nq NdWO 9#$ !$: \_.Jq JNWJ 9#$W

JKYN+ NYgM+ NYcN+ NcLK+ NOKc+ NJcJ+ NJMO+ NNgc+ dMN+ 0\R

4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo OdgWNcYdá /37$:o OdgWNcYg+

0T6> CX0 >3279$ iKcm 5*8!$*o cm /R?'3?!$32+ N 96t9#$+

JgL $9j \_.Nq KWg 9#$ !$: \_.Jq NNWL 9#$W

E\FDGDEPMKMQDO/92,1*8RDLD6:6DJKLKHKGD-,-.32*5.6DM;D:31-2,1D

MD61, E8(jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: KNm iOJWO

'8+^9:

E\FDWDI,-26:*DGD92,1*8DLD6:6DJKLKHKGD-,-.32*5.6DM;D

:31-2,1DMD61, E80jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2:

'8+^9:

9Dj !1 ! S5#.* 132#:+ *' KKoN+

q _Jdn i( q LWc+ >0>2_Oj+

;

9? q NgL R NgOn>+ ^N0 Z4\ iOLL 40H+ >X>2_Oj Ñ ^??9` q gWcg

R gWMM i9+ M0j+ gWMM R gWOc i9+ J0j+ gWOc R gWJd i9+ O0j+ gWJc

R gWLO i9+ M0j+ cWNc i1+ N0j+ MWYO i:+ A q NYWL 0H+ N0j+ MWcN i:.+

A q NYWL+ NWc 0H+ N0j+ MWJJ i:+ A q NYWL 0H+ N0j+ MWLK i::+ A q

NYWL+ NWc 0H+ N0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q

NKOWL+ NYOWY+ NMKWN+ NMMWJ+ NMNWL+ NOKWd+ NOLWY+ NJdWd+ NJdWY+

NJdWJ+ NJgWc+ NJgWO+ NJgWJ+ NJcWK+ NJMWK+ NNYWK+ NNJWc+ gNWK+

dNm iJcWL 9Dj !1 ! P*223S 132#:+ *' Kcoc+

q _NYn i( q

;

N

LWc+ >0>2_Oj 9? q dM R dYn>+ 0 Z4\ iMLL 40H+ >X>2_Oj Ñ

^??9` q gWJd Ä gWJN i9+ M0j+ gWJL Ä gWNO i9+ N0j+ gWLM i:+ A q

KWL 0H+ N0j+ YWgc i::+ A q KWL+ OWL 0H+ N0j+ YWcK i:+ A q JWK 0H+

N0j+ cWLY i1+ N0j+ MWcd i:+ A q NYWJ 0H+ N0j+ MWMd i:.+ A q NYWJ+

NWc 0H+ N0j+ MWNg i:+ A q NYWN 0H+ N0j+ MWLY i::+ A q NYWN+ NWd

0H+ N0j+ OWgL i1+ O0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9`

q NKJWK+ NYOWY+ NcgWN+ NMcWL+ NMOWO+ NJdWg+ NJdWJ+ NJYWK+

NJcWd+ NNgWg+ NNMWO+ NNMWJ+ NNNWd+ gNWK+ YMWg+ ccWg+ OgWJ+ A\

<

YMWg+ OYWM+ A\ ib<'j

^(9^RN` q OMMM+ NYgJ+ NYcN+ NcdN+

NMdc+ NOKM+ NOcc+ NJMO+ NNgJ+ gcd+ 0\R4- i]-Ajo (!2(W /3'o

i^4_Z!`^_jo OggWNNMdá /37$:o OOgWNNMK+ 0T6> CX0 >3279$

iKcm 5*8!$*o cm /R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NgWO

9#$ !$: \_.Jq JJWO 9#$W

<

ib<'j

^(9^RN` q OMMN+ NYgN+ NYMg+ NYNM+ NcKg+ NMKM+

NOKY+ NJON+ NNKM+ NLOL+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo

OONWLKMNá /37$:o OONWLKMJ+ 0T6> AA >3279$ iKcm 5*8!$*o

cm /R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NKWL 9#$ !$:

\_.Jq JOWd 9#$W

E\FDGDEHDU846.692,1*8FDLD6:6DJKLKHKGD-,-.32*5.6DM;D

:31-2,1DMD61, E8-jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2:

'8+⁹⁰

E\FDGDEJD!-2*892,1*8FDLD6:6DJKLKHKGD-,-.32*5.6DM;D:31-2,1D

MD61, E8%jW 0*8!$*t4;<] iKoNj !1 *27*$.+ h#*2: YJm iNKWL

'8+^9:

dMm iJMWK 9Dj !1 ! P*223S 132#:+ *' KJod+

q ROYn i( q

;

N

LWc+ >0>2_Oj+ 9? q Md R cLn>+ 0 Z4\ iMLL 40H+ >X>2_Oj Ñ

^??9` q gWJc Ä gWNY i9+ O0j+ gWNO Ä gWLg i9+ O0j+ YWKd Ä YWdK

i9+ J0j+ cWLd i1+ N0j+ MWYL i:+ A q NYWO 0H+ N0j+ MWMK i:.+ A q

NYWO+ NWc 0H+ N0j+ MWNK i:+ A q NYWJ 0H+ N0j+ MWLg i::+ A q NYWN+

NWd 0H+ N0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKOWL+

NYOWc+ NYNWg i:+ ^NA q JMcWO 0Hj+ NMKWL+ NMLWK i^M:+ A q OWN 0Hj+

9Dj !1 ! P*223S 132#:+ *' KKoN+

q RJNn i( q LWO+ >0>2_Oj+

;

9? q YM R YYn>+ ^N0 Z4\ iOLL 40H+ >X>2_Oj Ñ ^??9` q gWJO R

YWKY i9+ d0j+ cWOM i1+ N0j+ MWYJ i:+ A q NYWL 0H+ N0j+ MWcL i:.+

A q NYWL+ NWc 0H+ N0j+ MWNc i:+ A q NYWL 0H+ N0j+ MWLc i::+ A q

NYWL+ NWc 0H+ N0j+ OWJM Ä JWKd i9+ J0j+ NWOK i.+ A q gWc 0H+ O0j+

^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKJWK+ NYOWc+

NMdWg+ NMOWO+ NMNWN+ NOLWJ+ NJKWg+ NJdWg+ NJgWK+ NJYWd+ NJYWc+

NJcWK+ NJcWg+ NNYWK+ NNOWJ+ gNWK+ YMWg+ OJWM+ JcWg+ NcWY+ A\

NOLWc+ NJKWd i^O:+ A q dWN 0Hj+ NJdWO+ NJcWK+ NJMWg+NNgWL+ NNcWc

J

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ib<'j

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NOcM+ NJML+ NNgO+ gcc+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo

OOKWNNMdá /37$:o OJKWNNMg+ 0T6> CX0 >3279$ iKcm

5*8!$*o cm /R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NLWN 9#$

!$: \_.Jq NOWJ 9#$W

E\FDGDEHDI,-26:*DLKVD5/+,-2*892,1*8FDLD6:6DJKLKHKGD

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ACS Paragon Plus Environment

The Journal of Organic Chemistry

E\FDGDEHDI,-26:*92,1*8FDLD-2/6DJKLKHKGD-,-.32*5.6DM;D

Page 18 of 26

N

LWc+ >0>2_Oj+ 9? q NNY R NNdn>+ 0 Z4\ iOLL 40H+ >X>2_Oj Ñ

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i9+ J0j+ YWKJ R YWdJ i9+ J0j+ cWMJ i1+ N0j+ MWYJ i:+ A q NYWL 0H+

N0j+ MWcN i:.+ A q NYWL+ NWc 0H+ N0j+ MWNg i:+ A q NYWL 0H+ N0j+

MWLY i::+ A q NYWL+ NWc 0H+ N0j+ OWdJ i1+ O0j+ ^NO>Ö^N0Ü Z4\ igc

40H+ >X>2_Oj Ñ ^??9` q NKJWd+ NYMWO+ NcYWK+ NMKWN+ NOOWM+

NOLWL+ NJKWY+ NJdWJ+ NJgWg+ NJcWc+ NJcWM+ NJNWL+ NNYWO+ NNNWd+

1

2

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N0j+ OWgK Ä OWgL i9+ N0j+ OWgO i1+ O0j+ OWcJ i::+ A q NgWc+ JWL

0H+ N0j+ OWOK i::+ A q NYWL+ JWL 0H+ N0j+ OWNg i::+ A q NYWL+ JWL

0H+ N0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKNWO+

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^(9^RN` q OMMO+

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4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo OONWLKMNá /37$:o OONWLKMN+

0T6> CX0 >3279$ iKcm 5*8!$*o cm /R?'3?!$32+ N 96t9#$+

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9#$W

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i::+ A q NgWc+ JWL 0H+ N0j+ OWMJ i::+ A q NYWL+ JWL 0H+ N0j+ OWJL

i::+ A q NYWL+ JWL 0H+ N0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ

^??9` q NKNWO+ NYOWO+ NMKWJ+ NMMWg+ NMNWL+ NOKWY+ NOLWL+

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Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKNWM+ NYOWN+ NccWg+ NMKWN+

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i::+ A q NYWL+ JWL 0H+ N0j+ NWJM i1+ K0j+ ^NO>Ö^N0Ü Z4\ iNLL

40H+ >X>2_Oj Ñ ^??9` q NKNWO+ NYOWc+ NMdWg+ NMgWO+ NMcWY+

NJdWY+ NJgWd+ NJYWY+ NJYWM+ NJcWL+ NJMWY+ NNYWL+ NNMWc+ OdWc+

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ACS Paragon Plus Environment

Page 19 of 26

The Journal of Organic Chemistry

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>0>2_Oj+ 9? q NOO R NOcn>+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9`

q gWJc R gWJL i9+ N0j+ gWNY R gWLM i9+ c0j+ YWdO R YWgY i9+ J0j+

MWdK i1+ N0j+ OWgc i1+ O0j+ JWdY R JWgL i9+ J0j+ JWcM R JWMN i9+

J0j+ ^NO>Ö^N0Ü Z4\ igc 40H+ >X>2_Oj Ñ ^??9` q JLJWY+ NggWd+

NcdWc+ NcLWY+ NOYWK+ NONWJ+ NJKWM+ NJdWJ+ NJcWY+ NJMWc+ NNdWN+

<

NNgWJ+ NNMWL+ ccWO+ OgWg+ OOWY+ JcWg+ A\ ib<'j

^(9^RN` q

<

NNgWd+ NNMWJ+ ccWO+ OgWY+ OOWg+ JcWY+ A\ ib<'j

OMMN+ JKJK+ NgLL+ NYcJ+ NYNL+ NcLK+ NOdO+ NJMg+ NLON+ gcY+

0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo ONcWLKKNá /37$:o

ONcWLKKJ+ 0T6> CX0 >3279$ iKLm 5*8!$*o NLm /R

?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NYWK 9#$ !$: \_.Jq JgWg

9#$W

NYKd+ NYMK+ NYNN+ NcLK+ NMgL+ NOgg+ NJML+ NNgY+ NNcK+

NNNK+ NLOM+ NLNK+ dMM+ dJO+ 0\R4- i]-Ajo (!2(W /3'o

i^4_Z!`^_jo

OKOWLLKgtOKcWLLKgá

/37$:o

OKOWLLKdtOKcWLLKd+ 0T6> CX0 >3279$ iKLm 5*8!$*o NLm

/R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NKWO 9#$ !$: \_.Jq OJWY

9#$W

E\FDGDE9DS68*8FDLKGD5/2*5.60*0869,1-3P>R02.6+,1DMEJ;FD

61, E:'jW 0*8!$*t4;<] iJoNj !1 *27*$.+ h#*2: KJm iJcWM

'8+⁹_;⁰

E\FDGDEJD!-2*892,1*8FDWD+,-2*8DLKGD

5/2*5.60*0869,1-3P>R02.6+,1DMEJ;FD61,

9Dj !1 ! S5#.* 132#:+ *' KLWcoKWc+

q _Jdn i( q LWcL+

E:/jW

>0>2_Oj+ 9? q NMd R NcLn>+ ^N0 Z4\ iOLL 40H+ >X>2_Oj Ñ ^??9`

q gWJc Ä gWNd i9+ N0j+ gWNd Ä gWLL i9+ g0j+ MWKL i1+ N0j+ JWKM

Ä JWYM i9+ J0j+ JWcc Ä JWML i9+ J0j+ JWJg i1+ O0j+ ^NO>Ö^N0Ü Z4\

iNLL 40H+ >X>2_Oj Ñ ^??9` q JLJWY+ NggWK+ NcLWY+ NMNWY+

NOYWM+ NONWJ+ NJKWO+ NJdWO+ NJdWJ+ NJcWY+ NJMWM+ NNdWL+ NNgWJ+

0*8!$*t4;<] iJoNj !1 *27*$.+ h#*2: gdm iJOWg 9Dj !1 !

'8+^9:

S5#.* 132#:+ *' KgoO+

q _JLdn i( q LWOM+ >0>2_Oj+ 9? q NNd

;

N

R NJLn>+ 0 Z4\ iOLL 40H+ >X>2_Oj Ñ ^??9` q gWNK i::+ A q

gWc+ NWc 0H+ N0j+ gWNc R YWKc i9+ M0j+ YWdK i:+ A q gWc 0H+ N0j+

YWgM i1+ N0j+ cWNc i1+ N0j+ OWNd R JWdK i9+ J0j+ JWdK R JWYd i9+

J0j+ JWMd R JWOd i9+ J0j+ JWNK i1+ O0j+ NWOc i.+ A q gWc 0H+ O0j+

^NO>Ö^N0Ü Z4\ igc 40H+ >X>2_Oj Ñ ^??9` q JLJWO+ NggWK+ NMdWY+

NMJWY+ NMNWg+ NOcWJ+ NONWL+ NJKWK+ NJdWd+ NJdWg+ NJYWd+ NJYWM+

NJMWd+ NNdWM+ NNYWK+ OMWL+ OOWc+ JYWN+ JcWg+ JLWK+ NcWd+ A\

<

OdWN+ OOWY+ JcWg+ JNWJ+ A\ ib<'j

^(9^RN` q NgLJ+ NYcY+

NcgY+ NcLK+ NMdJ+ NMcc+ NOdJ+ NJMd+ NNYM+ NNNY+ NLNM+ gcc+

cJc+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo JKKWNLMLá /37$:o

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?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq NNWL 9#$ !$: \_.Jq NMWL

9#$W

i/#29j

^(9^RN` q JKJg+ NgLO+ NYcY+ NMKN+ NOgd+ NJcO+

NJON+ NNdd+ dNO+ gdg+ gYL+ 0\R4- i]-Ajo (!2(W /3'o

i^4_Z!`^_jo OJgWNOcYá /37$:o OJgWNOcY+ 0T6> CX0 >3279$

iKLm 5*8!$*o NLm /R?'3?!$32+ N 96t9#$+ JgL $9j \_.Nq dWc

9#$ !$: \_.Jq NLWK 9#$W

E\FDGDEHDE.*'.DO4-*8F92,1*8FDLKGD

5/2*5.60*0869,1-3P>R02.6+,1DMEJ;FD61,

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'8+⁹⁰

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q _Jcn i( q LWcL+ >0>2_Oj+ 9? q NMd

;

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5/2*5.60*0869,1-3P>R02.6+,1DMEJ;FD61,

R NcLn>+ ^N0 Z4\ iOLL 40H+ >X>2_Oj Ñ ^??9` q gWJK Ä gWJY i9+

N0j+ gWJc Ä gWNK i9+ J0j+ gWNY Ä gWLM i9+ c0j+ MWKJ i1+ N0j+

JWdK Ä JWYY i9+ J0j+ JWcM Ä JWMO i9+ J0j+ NWJY i1+ K0j+ ^NO>Ö^N0Ü

Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q JLJWY+ NgdWL+ NcLWg+ NMKWM+

NMNWM+ NONWO+ NJdWJ+ NJgWK+ NJcWc+ NJMWM+ NNdWN+ NNgWJ+ OgWK+

E:0jW

0*8!$*t4;<] iJoNj !1 *27*$.+ h#*2: KJm iJKWg 9Dj !1 !

'8+⁹⁰

S5#.* 132#:+ *' KOWcoYWc+

q RJcn i( q LWcL+ >0>2_Oj+ 9? q

;

NNM R NNYn>+ ^N0 Z4\ iOLL 40H+ >X>2_Oj Ñ ^??9` q gWJN Ä gWLK

i9+ N0j+ gWLK Ä YWKY i9+ J0j+ YWKJ Ä YWgK i9+ J0j+ YWgY Ä YWYO

i9+ J0j+ cWON i1+ N0j+ OWdO i1+ O0j+ OWYd i1+ O0j+ JWKJ Ä JWYg

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Ñ ^??9` q JLJWO+ NgKWJ+ NcYWd+ NcYWg+ NMMWY+ NOJWY+ NJKWM+

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<

OMWc+ OOWY+ ONWc+ JcWg+ A\ ib<'j

^(9^RN` q OMMc+ JKcd+

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<

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^(9^RN` q OMMJ+ JKJc+

NgLJ+ NYcc+ NMKJ+ NOdY+ NJMM+ NNgK+ NLOL+ 0\R4- i]-Ajo

(!2(W /3'o i^4_Z!`^_jo OMcWNLKgá /37$:o OMcWNLKY+ 0T6> CX0

ACS Paragon Plus Environment

The Journal of Organic Chemistry

Page 20 of 26

>3279$ iKLm 5*8!$*o NLm /R?'3?!$32+ N 96t9#$+ JgL $9j .3 !//3': .5* :*1#'*: (5'39*$*1W ;5* *$!$.#39*'#( '!.#31

1

\_.Nq JLWK 9#$ !$: \_.Jq JKWO 9#$W

S*'* :*.*'9#$*: "P 0T6> 3$ ! (5#'!2 1.!.#3$!'P ?5!1*W

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E\FDWDI,-2*8DGDE6D-68*8FDLKGD5/2*5.60*0869,1-3P>R02.6+,1D

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'8+⁹⁰

iJcWL 9Dj !1 ! P*223S 132#:+ *' KdoJ+

q _gMn i( q NWO+

KNm iJdWN 9Dj !1 ! P*223S 3#2+ *' KMoY+

q _JJn i( q LWcL+

;

N

>0>2_Oj+ 9? q cK R YNn>+ ^N0 Z4\ iOLL 40H+ >X>2_Oj Ñ ^??9` q

gWNg R YWdd i9+ Y0j+ YWgJ i1+ N0j+ cWNN i1+ N0j+ JWdd R JWYd i9+

J0j+ JWcg i1+ O0j+ JWMd R JWML i9+ J0j+ JWNK i1+ O0j+ ^NO>Ö^N0Ü

Z4\ igc 40H+ >X>2_Oj Ñ ^??9` q JLJWM+ NggWK+ NMdWY+ NMOWN+

NOcWd+ NOcWJ+ NONWL+ NOLWY+ NJKWK+ NJdWd+ NJYWY+ NJYWc+ NJMWc+

>0>2_O+ 0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q gWNY R YWKK i9+

M0j+ YWKO i:+ A q KWL 0H+ N0j+ YWYg i::+ A q KWL+ OWL 0H+ N0j+

YWcN i:+ A q OWL 0H+ N0j+ cWOL i1+ N0j+ OWYg i1+ O0j+ JWcY i1+ O0j+

JWML i:+ O0j+ JWNN i1+ O0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ

^??9` q NKKWJ+ NcdWO+ NcYWJ+ NMMWJ+ NMOWM+ NOMWY+ NONWJ+

NJKWO+ NJYWK+ NJYWd+ NJcWd+ NNgWN+ NNMWJ+ NNOWO+ NNOWJ+ ccWY+

<

NNdWO+ NNYWd+ OMWd+ OOWc+ JcWd+ JLWd+ JLWO+ A\ i/#29j

^(9^RN`

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^(9^RN` q JKON+ NYdJ+

<

q JKJM+ NgLO+ NYcc+ NMKN+ NOgg+ NJcO+ NNdK+ gdg+ gYN+ gOc+

0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo ONOWNNKKá /37$:o

ONOWNJLL+ 0T6> CX0 >3279$ iKLm 5*8!$*o NLm /R

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N 96t9#$+ JgL $9j \_.Nq NNWO 9#$ !$: \_.Jq NMWL 9#$W

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q _JLn i( q LWcL+

*27*$.+ h#*2: KYm iONWN 9Dj !1 ! P*223S 3#2+ *' KNWcodWc+

;

>0>2_Oj+ 9? q NNK R NJNn>+ ^N0 Z4\ iOLL 40H+ >X>2_Oj Ñ ^??9`

q gWJL Ä gWNN i9+ O0j+ gWNN Ä gWLc i9+ J0j+ gWLO Ä YWKY i9+

N0j+ YWKL Ä YWdJ i9+ J0j+ cWOJ i1+ N0j+ OWdL i1+ O0j+ JWKJ Ä

JWgN i9+ J0j+ JWMd i.+ A q cWL 0H+ J0j+ ^NO>Ö^N0Ü Z4\ igc 40H+

>X>2_Oj Ñ ^??9` q JLJWM+ NgdWK+ NcYWK+ NcLWc+ NOJWd+ NOLWc+

NJKWg+ NJdWN+ NJgWd+ NJcWO+ NJcWN+ NJNWL+ NNgWJ+ NNYWd+ NNNWd+

q RJNn i( q NWJc+ >0>2_O+ ^N0 Z4\ iMLL 40H+ >X>2_Oj Ñ ^??9` q

gWNd Ä gWNN i9+ N0j+ gWLg i::+ A q gWY+ NWY 0H+ N0j+ YWKM Ä YWdL

i9+ M0j+ YWYc i::+ A q dWK+ OWL 0H+ N0j+ cWcK i1+ N0j+ OWKY i1+

O0j+ OWgL i1+ O0j+ JWMc i1+ O0j+ JWLd i1+ O0j+ ^NO>Ö^N0Ü Z4\ iNLL

40H+ >X>2_Oj Ñ ^??9` q NKKWY+ NYLWN+ NcYWJ+ NccWM+ NMOWY+

NOMWc+ NJKWO+ NJdWL+ NJYWM+ NJNWY+ NNYWK+ NNOWJ+ NNOWN+ NNJWc+

^(9^RN` q OMMJ+ JKJM+

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^(9^RN` q JKOJ+

<

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q _MOn i( q

;

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gWM 0H+ N0j+ gWNg Ä gWLY i9+ O0j+ YWKM Ä YWdc i9+ J0j+ YWgg i1+

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O0j+ JWNN i1+ O0j+ NWON i.+ A q gWc 0H+ O0j+ ^NO>Ö^N0Ü Z4\ iNLL

40H+ >X>2_Oj Ñ ^??9` q NKKWY+ NcgWY+ NMgWN+ NMOWg+ NMLWY+

NOOWK+ NJKWY+ NJKWN+ NJdWd+ NJdWM+ NJYWK+ NJYWY+ NJMWg+ NNYWN+

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q _gYn i( q LWcL+ >0>2_Oj+ 9? q NJJ

;

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gWc+ NWc 0H+ N0j+ gWNM R gWLL i9+ O0j+ YWdK i:+ A q gWc 0H+ N0j+

YWgM i::+ A q KWL+ OWL 0H+ N0j+ YWMc i:+ A q OWL 0H+ N0j+ cWNY i1+

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JWcJ R JWOc i9+ J0j+ NWOM i.+ A q gWc 0H+ O0j+ ^NO>Ö^N0Ü Z4\ igc

40H+ >X>2_Oj Ñ ^??9` q JLJWO+ NgdWL+ NcYWK+ NMMWg+ NMJWJ+

NMNWg+ NJKWd+ NJdWd+ NJYWd+ NJYWM+ NJYWJ+ NNgWK+ NNgWd+ NNcWJ+

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!$: \_.Jq dWY 9#$W

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NLOc+ NLNg+ dNM+ 0\R4- i]-Ajo (!2(W /3'o i^4_Z!`^_jo

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q Rgn i( q

;

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gWd 0H+ N0j+ gWLg i:+ A q gWc 0H+ N0j+ gWLO i1+ N0j+ YWKO Ä YWdJ

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JWLK i1+ O0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKKWd+

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NJcWJ+ NJNWY+ NNcWK+ NNOWO+ NNLWK+ ccWg+ OMWJ+ JKWO+ JNWL+ JLWN+

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N 96t9#$+ JgL $9j \_.Nq gWd 9#$ !$: \_.Jq KWO 9#$W

ACS Paragon Plus Environment

Page 21 of 26

The Journal of Organic Chemistry

E\FDMDEHDEJDI,-26:*92,1*8FDJD+,-2*8DH;D02.6+,1DLD

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N0j+ cWON i1+ N0j+ MWLK Ä OWKg i9+ J0j+ OWLd Ä JWKL i9+ J0j+

JWMc i1+ O0j+ JWNg i1+ O0j+ NWOJ i.+ A q gWc 0H+ O0j+ NWLK i.+ A q

gWN 0H+ O0j+ ^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NYgWY+

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NJYWc+ NJYWO+ NJMWK+ NNYWN+ NLYWc+ YLWN+ OYWK+ JcWN+ JNWL+ NKWg+

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i9+ N0j+ gWNd Ä gWLc i9+ O0j+ YWKd Ä YWKJ i9+ J0j+ YWKN Ä YWdJ

i9+ J0j+ cWYJ i1+ N0j+ OWKc i1+ O0j+ JWMc i1+ O0j+ JWLK i1+ O0j+

^NO>Ö^N0Ü Z4\ iNLL 40H+ >X>2_Oj Ñ ^??9` q NKKWg+ NcKWY+

NccWc+ NMKWM+ NOMWY+ NJKWM+ NJdWK+ NJdWL+ NJgWc+ NJcWY+ NJMWc+

^(9^RN` q NgLd+ NYMJ+ NcKJ+ NMKK+

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NJYWL+ NJcWc+ NJcWO+ NJMWc+ NJOWg+ NNYWc+ NLYWM+ YLWN+ OcWY+

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q _JOn i( q

;

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NJgWcJ+ NJgWMc+ NJcWM+ NJcWO+ NJMWY+ NNYWO+ NLYWc+ YLWO+ MNWN+

^(9^RN` q NgNL+ NYMc+ NcdM+ NMdg+

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ACS Paragon Plus Environment

The Journal of Organic Chemistry

E\FD!-2*8 HDEHD+,-26:*92,1*8FDJD+,-2*8DH;D02.6+,1,DLD E\FDHDEJD!-2*892,1*8FDJKXD5/+,-2*8DH;D02.6+,1,DLD

Page 22 of 26

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ACS Paragon Plus Environment

Page 23 of 26

The Journal of Organic Chemistry

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ACS Paragon Plus Environment

The Journal of Organic Chemistry

Page 24 of 26

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ACS Paragon Plus Environment

Page 25 of 26

The Journal of Organic Chemistry

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ACS Paragon Plus Environment

The Journal of Organic Chemistry

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Article Doi

Phosphoric Acid Catalyzed Formation of Hydrogen-Bonded o-Quinone Methides. Enantioselective Cycloaddition with β-Dicarbonyl Compounds toward Benzannulated Oxygen Heterocycles

DOI: 10.1021/acs.joc.0c01375

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Article abstract of DOI:10.1021/acs.joc.0c01375

Full text of DOI:10.1021/acs.joc.0c01375

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