A general and facile approach for the synthesis of 2'-functionalized 1,1'-binapthyl-2-ols

Article abstract of DOI:10.1002/cjoc.201090276

A facile and efficient protocol for the synthesis of 2'-functionalized 1,1'-binaphthyl-2-ols has been developed. The C,O-dilithio reagent (2) generated by the reductive ring-opening of binaphthofuran (1) with lithium was treated with the corresponding electrophiles to give 2'-functionalized 1,1'-binaphthyl-2-ols including the halides (3), amine (4), acid (5), aldehyde (6), carbonate (7) or phosphonate (8), respectively, in moderate to good yields.

Full text of DOI:10.1002/cjoc.201090276

FULL PAPER
A General and Facile Approach for the Synthesis of
2'-Functionalized 1,1'-Binapthyl-2-ols†
Xie, Xiaomin*,a(谢小敏)
Ding, Linab(丁丽娜)
Ni, Gangc(倪刚)
Zhang, Zhaoguoa(张兆国)
Gao, Jinsheng*,b(高金胜)
a School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China
b School of Chemistry, Chemical Engineering and Materials, Heilongjiang University, Harbin, Heilongjiang
150080, China
c School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai
200237, China
A facile and efficient protocol for the synthesis of 2'-functionalized 1,1'-binaphthyl-2-ols has been developed.
The C,O-dilithio reagent (2) generated by the reductive ring-opening of binaphthofuran (1) with lithium was treated
with the corresponding electrophiles to give 2'-functionalized 1,1'-binaphthyl-2-ols including the halides (3), amine
(4), acid (5), aldehyde (6), carbonate (7) or phosphonate (8), respectively, in moderate to good yields.
Keywords 1,1'-binaphthyl-2-ol, chiral auxiliaries, lithiation, electrophile
Introduction
Heinicke and co-workers11 reported the synthesis of
2'-phosphanyl-1,1'-binaphthyl-2-ols from C,O-dilithio
reagents (2), in which the C,O-dilithio reagents was
generated by the reductive ring-opening of binaphtho-
furan (1) with lithium (Scheme 1). Up to now, only a
few reports for the preparation of dinaphthyl derivatives
by this method were published.3j,6b,12 Here we report an
improved convenient synthesis of 2'-functionalized
1,1'-binaphthyl-2-ols based on this reaction.
2'-Functionalized 1,1'-binaphthyl-2-ols have at-
tracted considerable interest of organic chemists due to
their useful applications. The axially chiral binaphthyl
skeletons of these compounds are efficient chiral auxil-
iaries in a variety of asymmetric reactions1 and in the
synthesis of optically active materials.2 The phosphines
of the skeleton are effective ligands in the transi-
tion-metal catalyzed C—C bond and C-hetero atom
bond forming reactions;3 the amines and their deriva-
tives have been extensively utilized in asymmetric reac-
tions as chiral ligands or organocatalysts;4 the acids are
used as good candidates for chiral derivatizing agents;5
and the alcohols are potential photochromic optical
triggers for liquid crystals.6 There are several methods
available for the synthesis of these binaphthyl com-
pounds, such as oxidative coupling reactions,7 nucleo-
philic aromatic substitution reactions,2a,8 transition
metal-catalyzed coupling reactions,9 as well as the
transformations from binaphthol or 2'-hydroxy-1,1-bina-
phthyl-2-carboxylic acid.10 However, these methods
show varying degrees of success as well as limitations
such as purification difficulties, requirements of noble
metal as the catalyst or expensive reagents, laborious
work-up, and/or harsh reaction conditions. Furthermore,
these methods are usually case-dependent. Therefore,
the development of a general and facile synthetic ap-
proach for the synthesis of 2'-functionalized 1,1'-bi-
naphthyl-2-ols has attracted our attention.
Scheme 1 The reductive ring-opening of binaphthofuran (1)
with lithium
Results and discussion
The C,O-dilithiated intermediate (2) was obtained by
C—O bond cleavage of binaphthofuran (1) with excess
of lithium at room temperature. According to the re-
ported procedure,11,12 we used Et2O as solvent in the
reductive ring-opening reaction. However, binaphtho-
furan (1) was not consumed completely, even when the
reaction time was prolonged. Because binaphthofuran is
poorly soluble in diethylether, we modified the proce-
dure by adding a toluene solution of binaphthofuran
*
E-mail: xiaominxie@sjtu.edu.cn; Fax: 0086-021-54748925; Tel: 0086-021-54748925
Received June 4, 2010; revised and accepted September 7, 2010.
Project supported by the National Natural Science Foundation of China (No. 20702030).
† Dedicated to the 60th Anniversary of Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.
1630
© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2010, 28, 1630— 1634

Synthesis of 2'-Functionalized 1,1'-Binapthyl-2-ols
dropwise to the suspension of lithium chip in diethyl
ether, the reaction was then complete at room tempera-
ture within 2.5 h.
desired to synthesize 2-amino-2'-hydroxy-1,1'-bina-
phthyl (NOBIN, 4), an important ligand and intermedi-
ate for other ligands in organic synthesis,4 whose syn-
thesis has been reported by several methods,7,9,10 but not
yet by electrophilic amination method.14 The dianion (2)
was treated with 2.0 equiv. of the electrophilic amina-
tion reagent, CH3ONH2/2CH3Li, at －50 ℃. Subse-
quent quenching with a saturated aqueous solution of
ammonium chloride afforded the expected product,
NOBIN, in 60% yield (Scheme 2).
2'-Halogen substituted 1,1'-binaphthyl-2-ols are im-
portant intermediates for MOP type ligands, however,
only a few synthetic methods were reported.2a,10d,10e,13 In
order to efficiently introduce a halogen atom, we inves-
tigated the reaction of the dianion (2) with several halo-
genating under various conditions. The results were
listed in Table 1. When the dianion (2) was reacted with
bromine, the expected 2'-bromo-derivative (3a) could
not be detected (Table 1, Entry 1). When NBS was the
electrophile only a trace of the product was obtained
(Table 1, Entry 2). When Br2CHCHBr2 as the electro-
phile, the expected product was obtained in 47% yield at
－15 ℃ (Table 1, Entry 3). Lowering the temperature
to －30 ℃ led to increased yield, but when the tem-
perature was further decreased to －78 ℃, no obvious
yield improvement was observed (Table 1, Entries 4 vs.
5). Under the optimized conditions, －30 ℃ and 1.1
equivalent of BrCH2CH2Br, 80% yield of the desired
product was obtained (Table 1, Entry 6). To synthesize
the iodide 3b, ICl was the electrophile of choice. At
－30 ℃, the dianion (2) was reacted with ICl to afford
3b in 42% yield. As the temperature was increased to
－15 ℃, the yield was increased to 53% (Table 1, En-
tries 8, 9). Higher temperature resulted in low yield, and
large excess of ICl is unnecessary in improving the
yield (Table 1, Entries 11, 12).
Scheme 2 Synthesis of NOBIN (4) by the reaction of the dian-
ion (2) with CH3ONH2/2CH3Li
We also investigated the reaction of the dianion (2)
with varying carbonyl compounds. The results are
shown in Scheme 3. Treatment of the dianion (2) with
CO2 (s) at －15 ℃ afforded the expected acid (5) in
69% yield simply by acidifying the reaction mixture,
filtration and washing. Similarly, the corresponding al-
dehyde (6) was obtained in satisfactory yield by treating
the dianion (2) with N,N-dimethylformamide, whereas
when the dianion (2) was treated with ethyl chlorofor-
mate under the same reaction conditions, only a trace of
Table 1 Synthesis of 2'-bromo(or iodo)-1,1'-binaphthyl-2-ols
Scheme 3 The reaction of the dianion (2) with carbonyl com-
pounds
Product and yield/
Entry
Electrophile
Temp.a/℃
%
1
2
Br2 (1.1 equiv.)
NBS (1.1 equiv.)
－15
－15
－15
－30
－78
－30
－15
－30
－15
r.t.
—
3a, 5.6
3a, 47
3a, 60
3a, 52
3a, 80
—
3
Br2CHCHBr2 (0.55 equiv.)
Br2CHCHBr2 (0.55 equiv.)
Br2CHCHBr2 (0.55 equiv.)
Br2CHCHBr2 (1.1 equiv.)
I2 (1.1 equiv.)
4
5
6
7
8
ICl (1.1 equiv.)
3b, 42
3b, 53
3b, 43
3b, 47
9
ICl (1.1 equiv.)
10
ICl (1.1 equiv.)
11
ICl (1.5 equiv.)
－15
a Refers to the addition of electrophiles to the dilithium salt and
the subsequent reaction temperature.
a: (i) CO2, (ii) H＋, yield 69%; b: (i) DMF, (ii) H＋, yield 83%; c: (i) CuI,
ClCOOEt , (ii) H＋, yield 71%; d: (i) CuI, ClPO(OEt)2, (ii) H＋, yield 59%.
Following the success of the synthesis of halides, we
Chin. J. Chem. 2010, 28, 1630— 1634
© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
1631

Xie et al.
FULL PAPER
the expected product was detected. However, when
catalytic amounts of CuI were added to the dianion (2),
followed by ethyl chloroformate at －15 ℃, the ex-
pected ester (7) was obtained in 71% yield. This strat-
egy is also applicable to the synthesis of the phospho-
nate which serves as a universal starting material for the
synthesis of MOP derivatives. In the presence of cata-
lytic amounts of CuI, the dianion (2) reacted with 1.1
equiv. of diethyl chlorophosphate at －15 ℃ to gener-
ate product (8) in 59% yield, whereas in the absence of
CuI only a 5% yield of the desired product was isolated
under otherwise identical reaction conditions.
132.7, 132.9, 134.1, 150.6.
Preparation of 2'-iodo-1,1'-binaphthyl-2-ol (3b)
By the procedure similar to that for the preparation
of 3a, ICl (3.3 g, 20.5 mmol) in Et2O (20 mL) was
added to the dianion (2, 18.6 mmol) solution at －15
℃, and kept stirring for 2 h at －15 ℃. 3b was ob-
1
tained in 53% yield (3.92 g). H NMR (CDCl3, 400
MHz) δ: 4.72 (s, 1H), 6.94 (d, J＝8.0 Hz, 1H), 7.25—
7.37 (m, 5H), 7.51—7.55 (m, 1H), 7.74 (d, J＝8.8 Hz,
1H), 7.88—7.95 (m, 3H), 8.10 (d, J＝8.4 Hz, 1H); 13C
NMR (CDCl3, 100 MHz) δ: 102.1, 118.0, 122.1, 124.0,
124.5, 126.8, 127.20, 127.23, 128.0, 128.4, 128.5, 129.3,
130.74, 130.77, 133.0, 133.5, 134.2, 136.3, 137.0,
150.6.
Conclusion
In summary, we have developed a simple and effi-
cient one-pot, two-step method for the synthesis of
various 2'-functionalized 1,1'-binaphthyl-2-ols by re-
ductive ring-opening of binaphthofuran (1) with lithium
to give the C,O-dilithium reagent (2), followed by re-
acting it with the corresponding electrophiles.
Preparation of NOBIN (4)
By the procedure similar to that for the preparation
of 3a, the dianion (2) solution was added dropwise to a
mixture, which was made by addition of methyllithium
(40 mL, 1.6 mol/L) to a suspension of O-methylhydro-
xylamine hydrochloride (2.18 g, 26.1 mmol) in Et2O, at
－50 ℃, and then the reaction mixture was warmed to
－15 ℃ and stirred for 2 h. 4 was obtained in 60%
yield (2.23 g). 1H NMR (DMSO, 400 MHz) δ: 4.56 (br,
2H), 6.74—6.77 (m, 1H), 6.94 (d, J＝8.4, 1H), 7.05—
7.11 (m, 2H), 7.17—7.27 (m, 3H), 7.37 (d, J＝8.8 1H),
7.72—7.74 (m, 2H), 7.86—7.91 (m, 2H), 9.33 (s, 1H);
13C NMR (DMSO, 100 MHz) δ: 112.0, 115.6, 119.2,
119.5, 121.5, 123.2, 124.2, 124.8, 126.4, 126.8, 127.7,
128.4, 128.7, 128.8, 129.2, 129.8, 134.4, 134.7, 144.7,
154.0
Experimental
General
All of reactions were carried out under a nitrogen
atmosphere in glassware that had been dried in an oven
and cooled under nitrogen. Toluene and Et2O were dis-
tilled under nitrogen from sodium and benzophenone.
All other chemicals were purchased commercially.
NMR (1H, 13C and 31P) spectra were recorded on a 400
MHz machine.
Preparation of 2'-hydroxy-1,1'-binapthyl-2-carbox-
ylic acid (5)
Typical procedure for the preparation of 2'-bromo-
1,1'-binaphthyl-2-ol (3a)
CO2 (s) was added in several portions to the dianion
(2) solution at －15 ℃, and then the mixture was
warmed to room temperature naturally and stirred over-
night. NaOH (2 mol/L, 80 mL) was added to the reac-
tion mixture carefully, and then the organic phase was
separated off. The aqueous phase was adjusted to pH＝
1 with 2 mol/L HCl, and the solid was precipitated. Af-
ter filtration, washing the cake with water, and dried, the
product 5 was obtained (4.03 g, 69%). 1H NMR (DMSO,
400 MHz) δ: 6.75 (d, J＝8.4 Hz, 1H), 7.12—7.35 (m,
5H), 7.55—7.60 (m, 1H), 7.84—7.88 (m, 2H), 8.02—
8.10 (m, 3H), 9.40 (s, 1H), 12.30 (br, 1H); 13C NMR
(DMSO, 100 MHz) δ: 118.89, 118.97, 123.0, 124.8,
126.8, 126.9, 127.3, 127.7, 128.1, 128.3, 128.5, 128.6,
128.7, 129.5, 131.1, 133.2, 134.9, 135.3, 136.9, 152.9,
169.3.
To a suspension of lithium chip (2.6 g, 0.372 mol,
10 equiv.) in Et2O (150 mL), a solution of binaphthofu-
ran (10.0 g, 37.3 mmol) in toluene (150 mL) was added
dropwise, and then the mixture was stirred at room
temperature for 2.5 h. After excess lithium was removed
by filtration, the solution of dianion (2) was cooled to
－30 ℃, and then C2H2Br4 (14.2 g, 41.0 mmol) in Et2O
(20 mL) was added dropwise. After the addition, the
mixture was stirred for 2 h at －30 ℃, and then it was
warmed to room temperature and stirred overnight. Af-
ter the reaction was quenched with 2 mol/L hydrochlo-
ric acid, the aqueous layer was extracted with Et2O (30
mL×2). The combined organic layer was dried over
anhydrous Na2SO4. The solvent was removed under
reduced pressure to give the crude product which was
purified by column chromatography on silica gel
[V(hexane)∶V(EA)＝20∶1] to give the product (3a)
Preparation of 2'-hydroxy-1,1'-binaphthyl-2-carbal-
dehyde (6)
1
(10.5 g, 80%). H NMR (CDCl3, 400 MHz) δ: 4.74 (s,
1H), 6.96 (d, J＝8.0 Hz, 1H), 7.24—7.27 (m, 2H), 7.32
—7.35 (m, 3H), 7.49—7.53 (m, 1H), 7.84—7.90 (m,
3H), 7.92—7.95 (m, 2H); 13C MNR (CDCl3, 100 MHz)
δ: 117.6, 118.2, 123.6, 124.2, 124.7, 126.0, 126.7, 126.9,
127.7, 128.2, 128.3, 129.0, 130.3, 130.4, 130.5, 131.8,
By the procedure similar to that for the preparation
of 3a, DMF (1.5 g, 20.5 mmol) in Et2O (20 mL) was
added to the dianion (2) solution at －15 ℃, and kept
stirring for 2 h at the same temperature. The product of
6 was obtained in 83% yield (4.83 g). 1H NMR (DMSO,
1632
www.cjc.wiley-vch.de
© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2010, 28, 1630— 1634

Synthesis of 2'-Functionalized 1,1'-Binapthyl-2-ols
400 MHz) δ: 6.76 (d, J＝8.0 Hz, 1H), 7.21—7.33 (m,
3H), 7.40—7.45 (m, 2H), 7.67—7.71 (m, 1H), 7.95 (d,
J＝8.5 Hz, 1H), 8.03 (d, J＝8.4 Hz, 2H), 8.11—8.18 (m,
2H), 9.62 (s, 1H), 9.94 (s, 1H); 13C NMR (DMSO, 100
MHz) δ: 113.9, 118.9, 122.6, 123.7, 124.7, 127.6, 127.8,
128.0, 128.5, 129.0, 129.30, 129.34, 129.9, 131.2, 132.5,
133.1, 135.3, 136.9, 142.8, 154.3, 193.1.
525.
2
(a) Ito, Y.; Miyake, T.; Hatano, S.; Sihma, R.; Ohara, T.;
Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880.
(b) Ito, Y.; Ohara, T.; Shima, R.; Suginome, M. J. Am.
Chem. Soc. 1996, 118, 9188.
(c) Ito, Y.; Miyake, T.; Ohara, T.; Suginome, M. Macro-
molecules 1998, 31, 1697.
(d) Rasmusson, T.; Martyn, L. J.; Chen, G.; Lough, A.; Oh,
M.; Yudin, A. K. Angew. Chem., Int. Ed. 2008, 47, 7009.
(a) García-Fortanet, J.; Kessler, F.; Buchwald, S. L. J. Am.
Chem. Soc. 2009, 131, 6676.
(b) Taylor, A. M.; Altman, R. A.; Buchwald, S. L. J. Am.
Chem. Soc. 2009, 131, 9900.
(c) Liu, Y.; Shi, M. Adv. Synth. Catal. 2008, 350, 122.
(d) Guan, X.; Jiang, Y.; Shi, M. Eur. J. Org. Chem. 2008,
12, 2150.
(e) Jiang, Y.; Shi, Y.; Shi, M. J. Am. Chem. Soc. 2008, 130,
7202.
(f) Ito, K.; Eno, S.; Saito, B.; Katsuki, T. Tetrahedron Lett.
2005, 46, 3981.
(g) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122,
976.
(h) Erre, G.; Enthaler, S.; Junge, K.; Gladiali, S.; Beller, M.
J. Mol. Catal. A: Chem. 2008, 280, 148.
(i) Takimoto, M.; Kajima, Y.; Sato, Y.; Mori, M. J. Org.
Chem. 2005, 70, 8605.
(j) Xie, X.; Zhang, T.; Zhang, Z. J. Org. Chem. 2006, 71,
6522.
Preparation of ethyl 2'-hydroxy-1,1'-binaphthyl-2-
carboxylate (7)
3
By the procedure similar to that for the preparation
of 3a, CuI (0.18 g, 0.93 mmol) was added to the dianion
(2) solution, and then ethyl chloroformate (1.5 g, 20.5
mmol) in Et2O (20 mL) was added to the solution at
－15 ℃ and kept stirring for 2 h at the same tempera-
ture. The product of 7 was obtained in 71% yield (4.52
1
g). H NMR (CDCl3, 400 MHz) δ: 0.70 (t, J＝6.8 Hz,
3H), 3.9 (q, J＝7.2 Hz, 2H), 4.85 (s, 1H), 6.88—6.91
(m, 1H), 7.17—7.21 (m, 1H), 7.26—7.36 (m, 4H), 7.55
—7.60 (m, 1H), 7.84 (d, J＝8.4 Hz, 1H), 7.90 (d, J＝
8.8 Hz, 1H), 7.97 (d, J＝8.4 Hz, 1H), 8.05—8.11 (m,
2H); 13C NMR (CDCl3, 100 MHz) δ: 13.5, 61.3, 117.9,
118.3, 123.6, 124.9, 126.4, 126.8, 127.4, 127.7, 128.2,
128.4, 128.5, 129.1, 129.4, 130.0, 131.4, 133.1, 133.6,
134.2, 135.5, 151.1, 168.2.
Preparation of diethyl 2'-hydroxy-1,1'-binaphthyl-2-
ylphosphonate (8)
By the procedure similar to that for the preparation
of 3a, CuI (0.18 g, 0.93 mmol) was added, and then di-
ethyl chlorophosphate (3.5 g, 20.5mmol) in Et2O (20
mL) was added to the dianion (2) solution at －15 ℃.
The reaction mixture was warmed to room temperature
naturally and stirred overnight. The product of 8 was
4
(a) Veldhuizen, J. V.; Garber, S. B.; Kingsbury, J. S.; Hov-
eyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954.
(b) Mikami, K.; Kataoka, S.; Wakabayashi, K.; Aikawa, K.
Tetrahedron Lett. 2006, 47, 6361.
(c) Kang, S.; Ko, D.; Kim, K. H.; Ha, D. Org. Lett. 2003, 5,
4571.
(d) Hu, Y.; Liang, X.; Wang, J.; Zheng, Z.; Hu, X. J. Org.
Chem. 2003, 68, 4542.
(e) Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed.
1999, 38, 3518.
(f) Singer, R. A.; Brock, J. R.; Carreira, E. M. Helv. Chim.
Acta 2003, 86, 1040.
(g) Zi, G.; Wang, Q.; Xiang, L.; Song, H. Dalton Trans.
2008, 43, 5930.
(h) Chianese, A. R.; Crabtree, R. H. Organometallics 2005,
24, 4432.
(i) Hu, Y.; Liang, X.; Zheng, Z., Hu, X. Tetrahedron:
Asymmetry 2003, 14, 2771.
1
obtained in 59% yield (4.46 g). H NMR (DMSO, 400
MHz) δ: 0.65 (t, J＝6.8 Hz, 3H), 0.97 (t, J＝6.8 Hz,
3H), 3.46—3.74 (m, 4H), 6.64 (d, J＝8.4 Hz, 1H), 7.10
—7.14 (m, 2H), 7.20—7.23 (m, 1H), 7.30—7.36 (m,
2H), 7.60 (t, J＝8.0 Hz, 1H), 7.83—7.90 (m, 2H), 8.04
—8.14 (m, 3H), 9.46 (s, 1H); 13C NMR (DMSO, 100
MHz) δ: 16.0, 16.1, 16.4, 16.5, 61.57, 61.61, 61.89,
61.94, 117.6, 118.8, 122.8, 125.4, 126.3, 126.6, 127.3,
127.5, 127.9, 128.0, 128.2, 128.3, 128.4, 128.6, 128.7,
129.4, 129.5, 130.0, 133.2, 133.4, 135.2, 135.4, 141.3,
141.4, 153.7; 31P NMR (DMSO, 162 MHz) δ: 18.19.
References
(j) Wang, C.; Jiang, Y.; Zhang, X.; Huang, Y.; Li, B.; Zhang,
G. Tetrahedron Lett. 2007, 48, 4281.
(k) Carreria, E.; Singer, R. A.; Lee, W. J. Am. Chem. Soc.
1994, 116, 8837.
(l) Carreria, E.; Lee, W.; Singer, R. A. J. Am. Chem. Soc.
1995, 117, 3649.
(m) Knölker, H.; Hermann, H. Angew. Chem., Int. Ed. Engl.
1996, 35, 341.
(n) Berrisford, D. J.; Bolm, C. Angew. Chem., Int. Ed. Engl.
1995, 34, 1717.
(o) Ko, D.; Kim, K. H.; Ha, D. Org. Lett. 2002, 4, 3759.
(a) Miyano, S.; Okada, S.; Hotta, H.; Takeda, M.; Kabuto,
1
(a) Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser,
M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005,
44, 5384.
(b) Blaser, H. Chem. Rev. 1992, 92, 935.
(c) Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P.
Synthesis 1992, 503.
(d) Ito, K.; Nishida, K.; Gotanda, T. Tetrahedron Lett. 2007,
48, 6147.
(e) Hasegawa, T.; Furusho, Y.; Katagiri, H.; Yashima, E.
Angew. Chem., Int. Ed. 2007, 46, 5885.
(f) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999,
5
Chin. J. Chem. 2010, 28, 1630— 1634
© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
1633

Xie et al.
FULL PAPER
C.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1989, 62, 1528.
(b) Narumi, F.; Hattori, T.; Yamabuki, W.; Kabuto, C.;
Kameyam, H. Tetrahedron: Asymmetry 2005, 16, 793.
(c) Latypov, S. K.; Aganov, A. V.; Tahara, S.; Fukushi, Y.
Tetrahedron 1999, 55, 7305.
(d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.;
Inoue, Y. J. Org. Chem. 1999, 64, 8660.
(e) Hattori, T.; Minato, Y.; Yao, S.; Finn, M. G.; Miyano, S.
Tetrahedron Lett. 2001, 42, 8015.
(c) Miyano, S.; Okada, S.; Suzuki, T.; Handa, S.; Hashimoto,
H. Bull. Chem. Soc. Jpn. 1986, 59, 2044.
(a) Moleele, S. S.; Michael, J. P.; de Koning, C. B. Tetra-
hedron 2008, 64, 10573.
(b) Uozumi, Y.; Matsuura, Y.; Arakawa, T.; Yamada, Y. M.
A. Angew. Chem., Int. Ed. 2009, 48, 2708.
(c) Bringmann, G.; Schöner, B.; Peters, K.; Peters, E.; von
Schnering, H. G. Liebigs Ann. Chem. 1994, 439.
9
10 (a) Sälinger, D.; Brückner, R. Synlett 2009, 109.
(b) Körber, K.; Tang, W.; Hu, X.; Zhang, X. Tetrahedron
Lett. 2002, 43, 7163.
6
7
(a) Burnham, K. S.; Schuster, G. B. J. Am. Chem. Soc. 1998,
120, 12619.
(b) Wang, B.; Li, M.; Xu, S.; Song, H.; Wang, B. Q.
Synthesis 2007, 1304.
(c) Shi, Y.; Wan, P. Chem. Commun. 1997, 273.
(a) Mahmoud, H.; Han, Y.; Segal, B. M.; Cai, L.
Tetrahedron: Asymmetry 1998, 9, 2035.
(b) Smrčina, M.; Lorenc, M.; Hanuš, V.; Sedmera, P.;
Kočovkŷ, P. J. Org. Chem. 1992, 57, 1917.
(c) Hon, S.; Li, C.; Kuo, J.; Barhate, N. B.; Liu, Y.; Wang,
Y.; Chen, C. Org. Lett. 2001, 3, 896.
(c) Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1999,
40, 1095.
(d) Clayden, J.; Kubinski, P. M.; Sammiceli, F.; Helliwell,
M.; Diorzaio, L. Tetrahedron 2004, 60, 4387.
(e) Kawabata, H.; Omura, K.; Uchida, T.; Katsuki, T. Chem.
Asian. J. 2007, 2, 248.
(f) Hamada, T.; Chieffi, A.; Åhmam, J.; Buchwald, S. L. J.
Am. Chem. Soc. 2002, 124, 1261.
(g) Uozumi, Y.; Tanahashi, A.; Lee, S.; Hayashi, T. J. Org.
Chem. 1993, 58, 1945..
(d) Smrčina, M.; Lorenc, M.; Hanuš, V.; Kočovský, P.
Synlett 1991, 231.
11 Kadyrov, R.; Heinicke, J.; Kinderman, M. K.; Heller, D.;
Fischer, C.; Selke, R.; Fischer, A. K.; Jones, P. G. Chem.
Ber. Recueil. 1997, 130, 1663.
12 Luo, Y.; Wang, F.; Zhu, G.; Zhang, Z. Tetrahedron:
Asymmetry 2004, 15, 17.
(e) Ding, K.; Xu, Q.; Wang, Y.; Liu, J.; Yu, Z.; Du, B.; Wu,
Y.; Koshima, H.; Matsuura, T. Chem. Commun. 1997, 693.
(f) Vyskočil, Š.; Smrčina, M.; Lorenc, M.; Hanuš, V.;
Polášek, M.; Kočovský, P. Chem. Commun. 1998, 585.
(a) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem.
Soc. Jpn. 1993, 66, 613.
8
13 Krasovskiy, A.; Gavryushin, A.; Knochel, P. Synlett 2005,
2691.
(b) Wilson, J. M.; Cram, D. J. J. Org. Chem. 1984, 49, 4930.
14 Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947.
(E1006041 Zhao, X.)
1634
www.cjc.wiley-vch.de
© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2010, 28, 1630— 1634