Recent advances in the asymmetric hydrosilylation of ketones, imines and electrophilic double bonds

被引：239

作者：

Riant, O ^{[1
]}

Mostefaï, N ^{[1
]}

Courmarcel, J ^{[1
]}

机构：

[1] Catholic Univ Louvain, Lab Chim Organ & Med, B-1348 Louvain, Belgium

来源：

SYNTHESIS-STUTTGART | 2004年 / 18期

关键词：

asymmetric catalysis; asymmetric hydrosilylation; chiral ligands; rhodium; titanium; zinc; conjugate addition; reduction;

D O I：

10.1055/s-2004-834932

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This literature review focuses on the recent advances in the asymmetric hydrosilylation of ketones and imines. New catalyst systems based on various transition metals, such as rhodium, titanium, zinc, copper and tin, combined with classical or new ligand structures, are presented. These systems lead to very effective and selective protocols for the reduction of prochiral ketones, imines and electrophilic double bonds.

引用

页码：2943 / 2958

页数：16

共 85 条

[1] Asymmetric conjugate reduction of α,β-unsaturated esters using a chiral phosphine-copper catalyst [J].

Appella, DH ;

Moritani, Y ;

Shintani, R ;

Ferreira, EM ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9473-9474

[2] Bis(oxazoline)titanium complexes as chiral catalysts for enantioselective hydrosilylation of ketones - A combined experimental and theoretical investigation [J].

Bandini, M ;

Bernardi, F ;

Bottoni, A ;

Cozzi, PG ;

Miscione, GP ;

Umani-Ronchi, A .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (15) :2972-2984

[3] Enantioselective reduction of ketones with triethoxysilane catalyzed by chiral bis-oxazoline titanium complexes [J].

Bandini, M ;

Cozzi, PG ;

Negro, L ;

Umani-Ronchi, A .

CHEMICAL COMMUNICATIONS, 1999, (01) :39-40

[4]

BASER HU, 2001, APPL CATAL A-GEN, V221, P119

[5] Chiral metallocenes.: 3.: The enantioselective reduction of C=X bonds (X = O or CH2) by the chiral ansa-metallocenes (R)- or (S)-[TiCl2(η5:η5-C5Me4SiMe2C5H3R*)] (R* = menthyl or neomenthyl) [J].

Beagley, P ;

Davies, PJ ;

Blacker, AJ ;

White, C .

ORGANOMETALLICS, 2002, 21 (26) :5852-5858

[6] New developments in zinc-catalyzed asymmetric hydrosilylation of ketones with PMHS [J].

Bette, V ;

Mortreux, A ;

Savoia, D ;

Carpentier, JF .

TETRAHEDRON, 2004, 60 (12) :2837-2842

[7] ASYMMETRIC SYNTHESES .20. ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH [RH(COD)CL]2 THIAZOLIDINE CATALYSTS [J].

BRUNNER, H ;

BECKER, R ;

RIEPL, G .

ORGANOMETALLICS, 1984, 3 (09) :1354-1359

[8] Chemo- and enantioselective hydrosilylation of carbonyl and imino groups. An emphasis on non-traditional catalyst systems [J].

Carpentier, JF ;

Bette, V .

CURRENT ORGANIC CHEMISTRY, 2002, 6 (10) :913-936

[9] ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH A CHIRAL TITANOCENE CATALYST [J].

CARTER, MB ;

SCHIOTT, B ;

GUTIERREZ, A ;

BUCHWALD, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :11667-11670

[10]

Courmarcel J, 2001, ISR J CHEM, V41, P231

← 1 2 3 4 5 6 7 8 9 →