Efficient Syntheses of (1R,2R)- and (1S,2S)-2-Amino-1-alkyl(or aryl)-1,3-propanediols by Regioselective Ring Opening of Aziridine-2-methanols

Full text of DOI:10.1021/jo961168z

J . Org. Chem. 1997, 62, 743-745
743
Sch em e 1. Red u ctive Clea va ge of th e Azir id in e
Efficien t Syn th eses of (1R,2R)- a n d
(1S,2S)-2-Am in o-1-a lk yl(or
Rin g
a r yl)-1,3-p r op a n ed iols by Regioselective
Rin g Op en in g of Azir id in e-2-m eth a n ols
Soo-Kyung Choi, J in-Soo Lee, J ung-Ho Kim,† and
Won Koo Lee*
Department of Chemistry, Sogang University,
Seoul 121-742, Korea
Recently, we reported that the C(3)-N bond in N-(R)-
(+)-(R-methylbenzyl)aziridine-2-methanol derivatives could
be reductively cleaved by catalytic hydrogenation with
high regioselectivity (Scheme 1). 10a,b We also found that
the substrates 2 could be prepared by stereoselective
addition of organolithiums to the configurationally stable
N-(S)-(-)-(R-methylbenzyl)aziridine-2(R)-carboxalde-
hyde 1. The C(3)-N bond of the aziridino secondary
alcohols 2 could also be reductively cleaved by catalytic
hydrogenation to provide â-amino alcohols 3 in high
yields.10c,d
Received J une 20, 1996
The asymmetric synthesis of 2-amino-1,3-propanediols1
is of current interest and concern. Compounds contain-
ing a 2-amino-1,3-propanediol subunit are important
constituents of broad-spectrum antibiotics, thiampheni-
col2 and florfenicol.3 The amino diol is also found in
sphingosines and dihydrosphingosines as the main struc-
tural unit.
The preparation of stereodefined â-hydroxy R-amino
acids is an important area because some of the acids can
be found in natural peptide antibiotics.4 Since the
carboxylic acid can be obtained from the corresponding
primary alcohol, the efficient preparation of optically pure
2-amino-1-substituted-1,3-propanediols is the key step for
the syntheses of â-hydroxy R-amino acids. A number of
hydroxy amino acids have emerged as key components
for pharmaceuticals5 and various protease inhibitors.6
Substituted aziridines have been utilized as substrates
in many important synthetic transformations.7 The ring
strain present in aziridines is responsible for the reactiv-
ity of N-activated aziridines toward nucleophiles.8 Many
examples of the regioselective ring opening by a variety
of nucleophiles have been reported.9 The products from
the ring-opening reactions can readily be transformed to
R- and â-amino acids as well as the more functionalized
hydroxy amino acids.
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† Agrochemical Lab, Hanwha Group Research & Engineering Cen-
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S0022-3263(96)01168-1 CCC: $14.00 © 1997 American Chemical Society

744 J . Org. Chem., Vol. 62, No. 3, 1997
Notes
Sch em e 3. Syn th etic Equ iva len ce betw een
Sch em e 2. Rin g Op en in g of Azir id in es by AcOH
Azir id in e-2-ca r boxa ld eh yd e a n d Ser in a l
ring-opening product 4 was achieved in high yields. We
were also able to isolate the regioisomer, C(2)-N opening
product, in less than 4% yield. We expected that the
acetyl group would readily migrate to the nitrogen upon
treating the reaction mixture with a base. However, the
acetyl group did not migrate and stayed on the oxygen.
The IR stretching frequency of the carbonyl (1740 cm-1
)
of 4a clearly indicates that it is an ester carbonyl. We
also tried to introduce the tert-butoxycarbonyl group on
the nitrogen, but the reaction did not proceed. We think
the steric bulkiness of the R-methylbenzyl group on the
nitrogen precludes the migration of the acetyl group or
the introduction of another electrophile. When we re-
moved the R-methylbenzyl group from the nitrogen, we
were able to isolate the acetyl-migrated N-acetamide 8a
which was indicated by the IR stretching frequency of
the carbonyl group (1657 cm-1). The acetyl protecting
group in 4 can readily be removed by KOH in refluxing
ethanol or by treating the compound with a catalytic
amount of concd HCl in refluxing aqueous THF to provide
7. The R-methylbenzyl group in 4 can also be removed
by catalytic hydrogenation to provide the N-acetamide
derivative 8.
The above experimental results show that the aziri-
dine-2(R)-carboxaldehyde 1 and its enantiomer 9 can
readily be converted to 2-amino-1-alkyl(or aryl)-1,3-
propanediols 7 and their enantiomers efficiently. There-
fore, the aziridine-2(R)-carboxaldehyde 1 and its enan-
tiomer 9 are synthetic equivalents of configurationally
stable D- and L-serinal, respectively (Scheme 3).
Ta ble 1. Rin g Op en in g of Azir id in es 2 by AcOH
yield of 4
absolute
entry
R
(% isolated)
configuration
2a
2b
2c
2d
2e
2f
phenyl
methyl
tert-butyl
91
87
85
85
85
95
88
87
89
91
(1R,2R)
(1R,2R)
(1R,2R)
(1R,2R)
(1R,2R)
(1R,2R)
(1S,2S)
(1R,2R)
(1S,2S)
(1S,2S)
1-naphthyl
2-methylphenyl
2-methoxyphenyl
2-naphthyl
3-methylphenyl
4-chlorophenyl
4-fluorophenyl
2ga
2h
2ia
2ja
a
2g,i,j are 1′(S)-aryl-N-[(R)-(+)-R-methylbenzyl]aziridine-2(S)-
methanols which can be obtained from the reaction of N-[(R)-(+)-
R-methylbenzyl]aziridine-2(S)-carboxaldehyde (9) with the corre-
sponding aryllithiums. Therefore, the products 4g,i,j have (1S,2S)
absolute configuration after the ring cleavage.
Exp er im en ta l Section
In this note, we report that the C(3)-N bond of 2 could
be cleaved by oxygen nucleophiles upon activating the
aziridine nitrogen with a protonic acid regioselectively
to provide 2-amino-1,3-propanediols as enantiomerically
pure forms.
Gen er a l. NMR spectra were recorded on spectrometers
operating at 200 and 300 MHz (1H) and at 50 and 75 MHz (13C)
in deuteriochloroform (CDCl3). Tetrahydrofuran and diethyl
ether were distilled from sodium-benzophenone ketyl at atmo-
spheric pressure immediately prior to use. Methylene chloride
was distilled from calcium hydride prior to use. All other
reagents and solvents used were reagent grade.
Resu lts a n d Discu ssion
Gen er a l P r oced u r e for Rin g Clea va ge. (1R,2R)-2-[N-
[(S)-r-m et h ylb en zyl]a m in o]-3-O-a cet yl-1-p h en yl-1,3-p r o-
p a n ed iol (4a ). To a solution of 1′(R)-phenyl-N-[(S)-R-methyl-
benzyl]aziridine-2(R)-methanol (2a ) (200 mg, 0.789 mmol) in 3.0
mL of methylene chloride was added 0.14 mL (2.37 mmol) of
acetic acid. The mixture was refluxed for 4 h and cooled to room
temperature. The mixture was then quenched with 0.5 mL of
saturated NaHCO3 solution. The organic layer was separated
and the aqueous layer was extracted with methylene chloride
(10 mL × 4). The combined organic extracts were dried over
anhydrous MgSO4, filtered, and concentrated in vacuo. Purifica-
tion by silica gel flash chromatography (EtOAc/n-hexane, 3:7)
provided 225 mg (91%) of (1R,2R)-2-[N-[(S)-R-methylbenzyl]-
amino]-3-O-acetyl-1-phenyl-1,3-propanediol (4a ) as a yellow oil.
An efficient conversion of N-(R or S)-(R-methylbenzyl)-
aziridine-2-methanol derivative 2 into [(1S,2S) or (1R,-
2R)]-2-amino-1-alkyl(or aryl)-1,3-propanediols 4 by a
straightforward reaction is shown in Scheme 2, and the
results are summarized in Table 1. The ring-opening
reaction seems to be accelerated upon protonation on the
nitrogen atom of the aziridine ring by AcOH to form an
aziridinium salt 5. Then the nucleophile, AcO-, attacks
the aziridine ring at the less sterically hindered C(3)
position to form an O-acetate as an ammonium salt 6.
The reaction proceeds smoothly at room temperature by
treating the substrate 2 in CH2Cl2 with 3 equiv of AcOH,
and refluxing the reaction mixture accelerates the ring-
opening process. On treatment of the reaction mixture
with saturated aqueous NaHCO3 solution, isolation of the
[R]22 ) -201.7° (c 1.0, CHCl3). IR (neat) 1740 cm-1 1H NMR
.
D
(CDCl3) δ 7.37-7.13 (m, 10H) , 4.43 (d, J ) 8.4 Hz, 1H), 4.27
(dd, J ) 11.9, 4.0 Hz, 1H), 3.94 (q, J ) 6.5 Hz, 1H), 3.73 (dd, J
) 11.8, 3.3 Hz, 1H), 2.62 (m, 1H), 2.09 (s, 3H), 1.38 (d, J ) 6.5

Notes
J . Org. Chem., Vol. 62, No. 3, 1997 745
Hz, 3H). 13C NMR (CDCl3) δ 170.6, 144.2, 141.3, 128.4, 128.1,
2.55 (m, 1H), 2.10 (s, 3H), 1.37 (d, J ) 6.5 Hz, 3H). 13C NMR
(CDCl3) δ 171.1, 144.2, 140.0, 133.6, 128.8, 128.6, 128.3, 127.6,
127.5, 127.1, 126.6, 61.8, 59.7, 55.2, 24.8, 20.5. Anal. Calcd for
C
19H23NO3: C, 72.8; H, 7.4; N, 4.5. Found: C, 72.6; H, 7.5; N,
4.5.
(1R,2R)-2-[N-[(S)-r-Met h ylb en zyl]a m in o]-3-O-a cet yl-1-
m eth yl-1,3-p r op a n ed iol (4b): [R]22D ) -117.8° (c 1.0, CHCl3).
IR (neat) 1740 cm-1 1H NMR (CDCl3) δ 7.33-7.24 (m, 5H) ,
127.0, 72.2, 61.3, 59.7, 55.2, 24.8, 20.6. Anal. Calcd for C19H22
-
ClNO3: C, 65.6; H, 6.4; N, 4.0. Found: C, 65.3; H, 6.4; N, 4.0.
(1S,2S)-2-[N-[(R)-r-Meth ylben zyl]a m in o]-3-O-a cetyl-1-(4-
flu or op h en yl)-1,3-p r op a n ed iol (4j): [R]22D ) +151.5° (c 0.99,
.
CHCl3). IR (CH2Cl2) 1740 cm-1 1H NMR (CDCl3) δ 7.38-7.22
.
4.31 (dd, J ) 11.8, 4.1 Hz, 1H), 4.05 (dd, J ) 11.3, 3.2 Hz, 1H),
4.05 (dd, J ) 11.3, 3.2 Hz, 1H), 4.02 (q, J ) 6.4 Hz, 1H), 3.56
(m, 1H), 2.29 (m, 1H), 2.09 (s, 3H), 1.36 (d, J ) 6.5 Hz, 3H),
1.09 (d, J ) 6.2 Hz, 3H). 13C NMR (CDCl3) δ 171.3, 144.7, 128.7,
127.4, 127.0, 66.5, 61.8, 59.3, 55.0, 25.1, 20.6, 19.1. Anal. Calcd
for C14H21NO3: C, 66.9; H, 8.4; N, 5.6. Found: C, 66.7; H, 8.5;
N, 5.6.
(m, 5H), 7.16-7.02(m, 2H), 7.00-6.88 (m, 2H), 4.40 (d, J ) 8.4
Hz, 1H), 4.27 (dd, J ) 12.0, 4.0 Hz, 1H), 3.95 (q, J ) 6.6 Hz,
1H), 3.71 (dd, J ) 11.9, 3.1Hz, 1H), 2.55 (m, 1H), 2.11 (s, 3H),
1.39 (d, J ) 6.5 Hz, 3H). 13C NMR (CDCl3) δ 171.2, 164.2, 160.9,
144.3, 137.3, 128.8, 128.7, 128.6, 127.5, 127.0, 115.4, 115.1, 72.3,
61.4, 59.8, 55.2, 24.9, 20.5. Anal. Calcd for C19H22FNO3: C,
68.9; H, 6.7; N, 4.2. Found: C, 68.6; H,6.7; N, 4.3.
(1R,2R)-2-[N-[(S)-r-Met h ylb en zyl]a m in o]-3-O-a cet yl-1-
(1R,2R)-2-[N-[(S)-r-Met h ylb en zyl]a m in o]-1-p h en yl-1,3-
p r op a n ed iol (7a ) To a solution of (1R,2R)-2-[N-[(S)-R-meth-
ylbenzyl]amino]-3-O-actyl-1-phenyl-1,3-propanediol 4a (112 mg,
0.357 mmol) in 1.8 mL of EtOH was added 49 mg (0.873 mmol)
of KOH. The mixture was refluxed for 2.5 h, concentrated in
vacuo, dissolved in 2 mL of water, and then neutralized by the
addition of 6 N HCl solution. The aqueous layer was extracted
with methylene chloride (10 mL × 4). The combined organic
extracts were dried over anhydrous MgSO4, filtered, and con-
centrated in vacuo. Purification by silica gel flash chromatog-
raphy (EtOAc/n-hexane, 7:3) provided 82 mg (85%) of (1R,2R)-
2-[N-[(S)-R-methylbenzyl]amino]-1-phenyl-1,3-propanediol (7a )
as a yellow oil. [R]22D ) -138.7° (c 1.0, CHCl3). 1H NMR (CDCl3)
δ 7.42-7.03 (m, 10H), 4.63 (d, J ) 7.4 Hz, 1H), 3.85 (q, J ) 6.5
Hz, 1H), 3.67 (dd, J ) 11.2, 3.8Hz, 1H), 3.31 (dd, J ) 11.2, 2.3
Hz, 1H), 2.53 (m, 1H), 1.36 (d, J ) 6.5 Hz, 3H). 13C NMR (CDCl3)
δ 144.8, 141.9, 128.7, 128.5, 127.9, 127.3, 126.9, 126.8, 73.7, 61.0,
59.1, 54.8, 24.7. Anal. Calcd for C17H21NO2: C, 75.3; H, 7.8;
N, 5.2. Found: C, 75.5; H, 7.8; N, 5.0.
ter t-bu tyl-1,3-p r op a n ed iol (4c): [R]22D ) -79.5° (c 1.0, CHCl3).
IR (CH2Cl2) 1738 cm-1 1H NMR (CDCl3) δ 7.32-7.23 (m, 5H),
.
4.25 (dd, J ) 11.6, 4.3 Hz, 1H), 4.02 (dd, J ) 11.8, 5.2 Hz, 1H),
3.95 (q, J ) 6.6 Hz, 1H), 2.93 (d, J ) 5.4Hz, 1H), 2.70 (m, 1H),
2.12 (s, 3H), 1.39 (d, J ) 6.6 Hz, 3H), 0.67 (s, 9H). 13C NMR
(CDCl3) δ 171.3, 144.2, 128.6, 127.5, 127.3, 75.2, 66.0, 56.0, 53.0,
34.7, 25.4, 24.2, 20.7. Anal. Calcd for C17H27NO3: C, 69.6; H,
9.3; N, 4.8. Found: C, 69.7; H, 9.5; N, 4.8.
(1R,2R)-2-[N-[(S)-r-Met h ylb en zyl]a m in o]-3-O-a cet yl-1-
(1-n a p h th yl)-1,3-p r op a n ed iol (4d ): [R]22 ) -148.5° (c 1.0,
D
CHCl3). IR (neat) 1740 cm-1
.
1H NMR (CDCl3) δ 7.81-7.72 (m,
3H), 7.48-7.15(m, 9H), 5.13 (d, J ) 8.1 Hz, 1H), 4.27 (dd, J )
11.7, 4.4 Hz, 1H), 3.87 (q, J ) 6.3 Hz, 1H), 3.69 (dd, J ) 11.8,
3.6Hz, 1H), 3.07 (m, 1H), 2.09 (s, 3H), 1.38 (d, J ) 6.5 Hz, 3H).
13C NMR (CDCl3) δ 170.3, 144.1, 136.7, 133.6, 130.4, 128.4,
128.0,127.9, 126.7, 126.4, 125.3, 124.9, 124.7, 123.2, 70.6, 62.6,
58.0, 55.3, 24.2, 20.3. Anal. Calcd for C23H25NO3: C, 76.0; H,
6.9; N, 3.9. Found: C, 75.9; H, 6.9; N, 3.8.
(1R,2R)-2-[N-[(S)-r-Met h ylb en zyl]a m in o]-3-O-a cet yl-1-
(2-m eth ylp h en yl)-1,3-p r op a n ed iol (4e): [R]20 ) -136.2° (c
D
On e-P ot P r oced u r e fr om 2a . To a solution of 1′(R)-phenyl-
N-[(S)-R-methylbenzyl]aziridine-2(R)-methanol (2a) (50 mg, 0.197
mmol) in 0.66 mL of methylene chloride was added 34 µL (0.592
mmol) of acetic acid. The mixture was refluxed for 4 h and then
concentrated in vacuo. The residue was dissolved in aqueous
THF (0.66 mL) and a catalytic amount of concd HCl was added.
The mixture was refluxed for 8 h, and the reaction mixture was
neutralized by the addition of saturated NaHCO3 solution. The
aqueous layer was extracted with EtOAc (10 mL × 4). The
combined organic extracts were dried over anhydrous MgSO4,
filtered, and concentrated in vacuo. Purification by silica gel
flash chromatography (EtOAc/n-hexane, 1:1) provided 41 mg
(77%) of (1R,2R)-2-[N-[(S)-R-methylbenzyl]amino]-1-phenyl-1,3-
propanediol (7a ) as a yellow oil.
1.0, CHCl3). IR (CH2Cl2) 1740 cm-1
.
1H NMR (CDCl3) δ 7.34-
7.04 (m, 9H) , 4.73 (d, J ) 8.05 Hz, 1H), 4.29 (dd, J ) 11.7, 4.5
Hz, 1H), 3.91 (q, J ) 6.5 Hz, 1H), 3.67 (dd, J ) 11.7, 3.3 Hz,
1H), 2.72 (m, 1H), 2.17 (s, 3H), 2.07 (s, 3H), 1.36 (d, J ) 6.4 Hz,
3H). 13C NMR (CDCl3) δ 171.2, 144.7, 139.6, 135.6, 130.7, 128.7,
127.5, 127.3, 127.2 127.0, 126.2, 69.4, 62.2, 58.3, 55.2, 24.8, 20.6,
18.7. Anal. Calcd for C20H25NO3: C, 73.4; H, 7.7; N, 4.3.
Found: C,73.0; H, 7.7; N, 4.2.
(1R,2R)-2-[N-[(S)-r-Met h ylb en zyl]a m in o]-3-O-a cet yl-1-
(2-m eth oxyp h en yl)-1,3-p r op a n ed iol (4f): [R]22D ) -149.1° (c
1.0, CHCl3). IR (CH2Cl2) 1738 cm-1 1H NMR (CDCl3) δ 7.34-
.
7.13 (m, 7H) , 6.88 (t, J ) 7.4Hz, 1H), 6.77 (d, J ) 8.3 Hz, 1H),
4.82 (d, 7.32Hz, 1H), 4.15 (dd, J ) 11.6, 4.7 Hz, 1H), 3.88 (dd, J
) 8.0, 3.3 Hz, 1H), 3.86 (q, J ) 6.2 Hz, 1H), 3.63 (s, 3H), 2.81
(dt,J ) 7.3, 4.3Hz, 1H), 2.06 (s, 3H), 1.35 (d, J ) 6.6 Hz, 3H).
13C NMR (CDCl3) δ 170.6, 156.5, 144.8, 129.8, 128.2, 127.8,
127.6, 126.7, 126.6, 120.5, 110.3, 68.1, 63.1, 58.2, 55.5, 54.9, 24.6,
20.6. Anal. Calcd for C20H25NO4: C, 70.0; H, 7.3; N, 4.1.
Found: C,69.7; H, 7.3; N, 4.0.
(1R,2R)-2-(N-Acetylam in o)-1-ph en yl-1,3-pr opan ediol (8a).
To a solution of (1R,2R)-2-[N-[(S)-R-methylbenzyl]amino]-3-O-
acetyl-1-phenyl-1,3-propanediol (4a ) (107 mg, 0.341 mmol) in
0.86 mL of EtOAc:MeOH (1:1) was added 22 mg of Pd(OH)2. The
mixture was stirred under a balloon pressure of hydrogen for 2
days at room temperature. The reaction mixture was filtered
and concentrated. Purification by silica gel flash chromatogra-
phy (MeOH/methylene chloride, 7:93) provided 65 mg (92%) of
(1R,2R)-2-(N-acetylamino)-1-phenyl-1,3-propanediol (8a ) as a
(1S,2S)-2-[N-[(R)-r-Meth ylben zyl]a m in o]-3-O-a cetyl-1-(2-
n aph th yl)-1,3-pr opan ediol (4g): [R]22D )+113.7° (c 1.0, CHCl3).
IR (CH2Cl2) 1738 cm-1 1H NMR (CDCl3) δ 7.80-7.65 (m, 5H),
.
7.46-7.34(m, 3H), 7.28-7.20 (m, 6H), 4.60 (d, J ) 8.1 Hz, 1H),
4.30 (dd, J ) 11.8, 4.3 Hz, 1H), 3.94 (q, J ) 6.6 Hz, 1H), 3.77
(dd, J ) 11.8, 3.4Hz, 1H), 2.74 (m, 1H), 2.08 (s, 3H), 1.37 (d, J
) 6.6 Hz, 3H). 13C NMR (CDCl3) δ 171.2, 144.4, 139.0, 133.3,
128.8, 128.3, 128.1, 127.8, 127.5, 127.1, 126.2, 126.0, 124.6, 73.1,
61.7, 59.6, 55.3, 24.9, 20.6. Anal. Calcd for C23H25NO3: C, 76.0;
H, 6.9; N, 3.9. Found: C, 76.0; H, 6.9; N, 3.8.
white foam. [R]22 ) -41.0° (c 1.0, CHCl3). IR (CH2Cl2) 1657
D
cm-1 1H NMR (CD3OD) δ 7.42-7.23 (m, 5H) , 4.92 (d, J ) 4.4
.
Hz, 1H), 4.09 (m,1H), 3.68 (dd, J ) 10.9, 6.1 Hz, 1H), 3.46 (dd,
J ) 10.9, 5.9 Hz, 1H), 1.90 (s, 3H). 13C NMR (CDCl3) δ 171.8,
141.3, 128.6, 128.0, 126.0, 73.7, 63.4, 56.5, 22.9 Anal. Calcd for
C
11H15NO3: C, 63.1; H, 7.2; N, 6.7. Found: C, 63.1; H, 7.4; N,
6.6.
(1R,2R)-2-[N-[(S)-r-Met h ylb en zyl]a m in o]-3-O-a cet yl-1-
(3-m eth ylp h en yl)-1,3-p r op a n ed iol (4h ): [R]22 ) -120.4° (c
D
0.98, CHCl3). IR (CH2Cl2) 1738 cm-1
.
1H NMR (CDCl3) δ 7.37-
Ack n ow led gm en t. This work was supported by the
Korea Science and Engineering Foundation (through
OCRC) and the Ministry of Education (BSRI-3412-96).
6.95 (m, 9H) , 4.40 (d, J ) 8.4 Hz, 1H), 4.27 (dd, J ) 11.9, 4.0
Hz, 1H), 3.94 (q, J ) 6.6 Hz, 1H), 3.74 (dd, J ) 11.8, 3.3 Hz,
1H), 2.63 (m, 1H), 2.27 (s, 3H), 2.10 (s, 3H), 1.37 (d, J ) 6.6 Hz,
3H). 13C NMR (CDCl3) δ 171.2, 144.4, 141.3, 138.1, 128.8, 128.7,
128.3, 127.5, 127.4, 127.0, 124.1, 73.0, 61.6, 59.7, 55.2, 24.9, 21.1,
20.6. Anal. Calcd for C20H25NO3: C, 73.4; H, 7.7; N, 4.3.
Found: C, 73.2; H, 7.8; N, 4.3.
Su p p or tin g In for m a tion Ava ila ble: IR, 1H, and 13C
NMR spectra for 4a -j, 7a , and 8a (35 pages). This material
is contained in libraries on microfiche, immediately follows this
article in the microfilm version of the journal, and can be
ordered from the ACS; see any current masthead page for
ordering information.
(1S,2S)-2-[N-[(R)-r-Meth ylben zyl]a m in o]-3-O-a cetyl-1-(4-
ch lor op h en yl)-1,3-p r op a n ed iol (4i): [R]22 ) +114.5° (c 1.0,
D
CHCl3). IR (CH2Cl2) 1740 cm-1
.
1H NMR (CDCl3) δ 7.40-7.06
(m, 9H), 4.39 (d, J ) 8.1 Hz, 1H), 4.27 (dd, J ) 12.0, 4.1 Hz,
1H), 3.93 (q, J ) 6.6 Hz, 1H), 3.73 (dd, J ) 11.8, 3.3Hz, 1H),
J O961168Z