Highly efficient synthesis of chiral β-hydroxy sulfides with high enantiomeric purity via CBS-oxazaborolidine-catalyzed borane reduction

被引：24

作者：

Cho, BT ^{[1
]}

Choi, OK ^{[1
]}

Kim, DJ ^{[1
]}

机构：

[1] Hallym Univ, Dept Chem, Chunchon 200702, South Korea

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 07期

基金：

新加坡国家研究基金会;

关键词：

D O I：

10.1016/S0957-4166(02)00193-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A simple and efficient synthesis of chiral beta-hydroxy p-tolylsulfides with high enantiomeric purity by CBS-oxazaborolidine-catalyzed asymmetric borane reduction of beta-keto p-tolyisulfides using N-ethyl-N-isopropylaniline-borane complex as the borane carrier is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：697 / 703

页数：7

相关论文

共 57 条

[41]

SEYDENPENNE, 1997, REDUCTIONS ALUMINO B

[42] Highly stereocontrolled access to 1,1,1-trifluoro-2,3-epoxypropane via lipase-mediated kinetic resolution of 1,1,1-trifluoro-3-(phenylthio)propan-2-ol and its application [J].

Shimizu, M ;

Sugiyama, K ;

Fujisawa, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (09) :2655-2659

[43] Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides:: versatile synthons for enantiopure β-hydroxy sulfoxides [J].

Singh, S ;

Kumar, S ;

Chimni, SS .

TETRAHEDRON-ASYMMETRY, 2001, 12 (17) :2457-2462

[44] ASYMMETRIC-SYNTHESIS OF CHIRAL SPIROACETALS FROM CHIRAL DIKETODISULFOXIDES - 2,8-DIMETHYL-1,7-DIOXASPIRO [5,5]UNDECANE [J].

SOLLADIE, G ;

HUSER, N .

TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :255-260

[45] ASYMMETRIC-SYNTHESIS OF THE C-3/C-9 FRAGMENT OF (-)-ASPICILIN [J].

SOLLADIE, G ;

FERNANDEZ, I ;

MAESTRO, C .

TETRAHEDRON LETTERS, 1991, 32 (04) :509-512

[46] REDUCTION OF BETA-KETO SULFOXIDES - A HIGHLY EFFICIENT ASYMMETRIC-SYNTHESIS OF BOTH ENANTIOMERS OF ALLYLIC ALCOHOLS [J].

SOLLADIE, G ;

DEMAILLY, G ;

GRECK, C .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1552-1554

[47] REDUCTION OF CHIRAL BETA-HYDROXY SULFOXIDES - APPLICATION TO THE SYNTHESIS OF BOTH ENANTIOMERS OF 4-SUBSTITUTED BUTENOLIDES [J].

SOLLADIE, G ;

FRECHOU, C ;

DEMAILLY, G ;

GRECK, C .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1912-1914

[48] ASYMMETRIC-SYNTHESIS OF ORSELLINIC ACID TYPE MACROLIDES - THE EXAMPLE OF LASIODIPLODIN [J].

SOLLADIE, G ;

RUBIO, A ;

CARRENO, MC ;

RUANO, JLG .

TETRAHEDRON-ASYMMETRY, 1990, 1 (03) :187-198

[49] REDUCTION OF BETA-HYDROXYSULFOXIDES - APPLICATION TO THE SYNTHESIS OF OPTICALLY-ACTIVE EPOXIDES [J].

SOLLADIE, G ;

DEMAILLY, G ;

GRECK, C .

TETRAHEDRON LETTERS, 1985, 26 (04) :435-438

[50] ASYMMETRIC-SYNTHESIS OF (S)-ZEARALENONE DIMETHYL ETHER, AN ORSELLINIC ACID TYPE MACROLIDE [J].

SOLLADIE, G ;

MAESTRO, MC ;

RUBIO, A ;

PEDREGAL, C ;

CARRENO, MC ;

RUANO, JLG .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2317-2322

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