Conjugate reduction of α,β-unsaturated ketones with hydrosilane mediated by copper(I) salt

被引：52

作者：

Mori, A ^{[1
]}

Fujita, A ^{[1
]}

Kajiro, H ^{[1
]}

Nishihara, Y ^{[1
]}

Hiyama, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Resources Utilizat Res Lab, Yokohama, Kanagawa 2268503, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 15期

关键词：

copper and compounds; ketones; reduction; silicon and compounds;

D O I：

10.1016/S0040-4020(99)00141-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reduction of several alpha,beta-unsaturated ketones with dimethylphenylsilane and 10-100 mol% of CuF(PPh3)(3). 2EtOH or CuCl/PPh3/Bu4NF proceeds in a 1,4-selective manner to give the corresponding saturated ketones in up to >99% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4573 / 4582

页数：10

共 32 条

[1]

Auner N., 1994, ORGANOSILICON CHEM M

[2]

Collman J.P., 1987, PRINCIPLES APPL ORGA

[3]

Colvin E. W., 1988, SILICON REAGENTS ORG

[4] 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

[5] COORDINATION STABILIZED COPPER(I) FLUORIDE - CRYSTAL AND MOLECULAR-STRUCTURE OF FLUOROTRIS(TRIPHENYLPHOSPHINE)COPPER(I).ETHANOL (1-2), CU(PPH3)3F.2ETOH [J].

GULLIVER, DJ ;

LEVASON, W ;

WEBSTER, M .

INORGANICA CHIMICA ACTA-ARTICLES, 1981, 52 (02) :153-159

[6] PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF ORGANOMETALLOIDS THROUGH ACTIVATION WITH FLUORIDE-ION [J].

HIYAMA, T ;

HATANAKA, Y .

PURE AND APPLIED CHEMISTRY, 1994, 66 (07) :1471-1478

[7] DIASTEREOGENIC ADDITION OF CROTYLMETAL COMPOUNDS TO ALDEHYDES [J].

HOFFMANN, RW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (08) :555-566

[8]

HOSOMI A, 1976, TETRAHEDRON LETT, P1295

[9] Copper(I) salt promoted homo-coupling reaction of organosilanes [J].

Ikegashira, K ;

Nishihara, Y ;

Hirabayashi, K ;

Mori, A ;

Hiyama, T .

CHEMICAL COMMUNICATIONS, 1997, (11) :1039-1040

[10] Studies on organosilicon chemistry. 138. Generation of a reducing reagent from copper(I) salt and hydrosilane. New practical method for conjugate reduction [J].

Ito, H ;

Ishizuka, T ;

Arimoto, K ;

Miura, K ;

Hosomi, A .

TETRAHEDRON LETTERS, 1997, 38 (51) :8887-8890

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