Catalytic activation of trichlorosilane for efficient and stereoselective reduction of ketones

被引：69

作者：

Iwasaki, F

Onomura, O

Mishima, K

Maki, T

Matsumura, Y

机构：

[1] Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 8128151, Japan

[2] Tokuyama Corp, Tsukuba Res Lab, Tsukuba, Ibaraki 3004247, Japan

[3] Nagasaki Univ, Fac Pharmaceut Sci, Nagasaki 8528521, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 42期

关键词：

asymmetric reaction; reduction; silicon halides; ketones; substituent effects;

D O I：

10.1016/S0040-4039(99)01554-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Some kinds of N-formyl cyclic amine derivatives were found to be effective activators for trichlorosilane to reduce ketones. Namely, a catalytic amount of these activators were sufficient to complete the reduction of ketones with trichlorosilane, and the reduction of ketones by trichlorosilane with optically active activators gave enantiomerically enriched sec-alcohols in some extent of optical yields (up to 51% ee). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：7507 / 7511

页数：5

相关论文

共 14 条

[1] ASYMMETRIC-SYNTHESIS OF USEFUL TERPENOIDS [J].

AKUTAGAWA, S .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1986, 44 (06) :513-518

[2] A NEW METHOD OF FORMING CARBON-SILICON BOND . REDUCTIVE SILYLATION OF CARBONYL COMPOUNDS [J].

BENKESER, RA ;

SMITH, WE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (06) :1556-&

[3] SELECTIVE REDUCTION OF CARBONYL-COMPOUNDS BY HETEROGENEOUS CATALYSIS ON SALT SURFACES [J].

BOYER, J ;

CORRIU, RJP ;

PERZ, R ;

REYE, C .

TETRAHEDRON, 1981, 37 (11) :2165-2171

[4] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES [J].

CHUIT, C ;

CORRIU, RJP ;

REYE, C ;

YOUNG, JC .

CHEMICAL REVIEWS, 1993, 93 (04) :1371-1448

[5] Alkoxy-directed radical reductions of ketones using trichlorosilane [J].

Enholm, EJ ;

Schulte, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) :2610-2611

[6] HIGHLY DIASTEREOCONTROLLED REDUCTION OF KETONES BY MEANS OF HYDROSILANES - PRACTICAL SYNTHESIS OF OPTICALLY-ACTIVE 1,2-DIOLS AND 2-AMINO ALCOHOLS OF THREO OR ERYTHRO CONFIGURATION [J].

FUJITA, M ;

HIYAMA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (16) :4629-4630

[7] PENTACO-ORDINATE SILICON-COMPOUNDS IN SYNTHESIS - CHEMO-SELECTIVE AND STEREOSELECTIVE REDUCTION OF CARBONYL-COMPOUNDS USING TRIALKOXY-SUBSTITUTED SILANES AND ALKALI-METAL ALKOXIDES [J].

HOSOMI, A ;

HAYASHIDA, H ;

KOHRA, S ;

TOMINAGA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (18) :1411-1412

[8]

KIRA M, 1987, Journal of Organic Chemistry, V52, P949

[9] Trichlorosilane-dimethylformamide (Cl3SiH-DMF) as an efficient reducing agent. Reduction of aldehydes and imines and reductive amination of aldehydes under mild conditions using hypervalent hydridosilicates [J].

Kobayashi, S ;

Yasuda, M ;

Hachiya, I .

CHEMISTRY LETTERS, 1996, (05) :407-408

[10] PENTACO-ORDINATE ORGANO-SILICON COMPOUNDS IN SYNTHESIS - ASYMMETRIC REDUCTION OF CARBONYL-COMPOUNDS WITH HYDROSILANES CATALYZED BY CHIRAL BASES [J].

KOHRA, S ;

HAYASHIDA, H ;

TOMINAGA, Y ;

HOSOMI, A .

TETRAHEDRON LETTERS, 1988, 29 (01) :89-92