The highly enantioselective transformation of silylketenes into α-silylthioesters catalysed by cinchona alkaloids

被引：12

作者：

Blake, AJ

Friend, CL

Outram, RJ

Simpkins, NS

Whitehead, AJ

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] GlaxoWellcome, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 15期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(01)00304-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of silylketenes with thiophenol, mediated by cinchona alkaloid catalysts, proceeds to give alpha -silylthioester products in good chemical yield and with enantiomeric excess values in the range 79-93%. The absolute configuration of one of the thioester products was determined by X-ray diffraction. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2877 / 2881

页数：5

相关论文

共 17 条

[1] GENERAL KETONE SYNTHESIS - REACTION OF ORGANOCOPPER REAGENTS WITH S-ALKYL AND S-ARYL THIOESTERS [J].

ANDERSON, RJ ;

HENRICK, CA ;

ROSENBLU.LD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (11) :3654-3655

[2] EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF ALLYLSILANES BY WITTIG OLEFINATION OF ALPHA-SILYLALDEHYDES [J].

BHUSHAN, V ;

LOHRAY, BB ;

ENDERS, D .

TETRAHEDRON LETTERS, 1993, 34 (32) :5067-5070

[3] PHENYL(TRIMETHYLSILYL)KETENE - SOME KETENE REACTIONS WITH DIAZOMETHANE [J].

BRADY, WT ;

CHENG, TC .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 137 (03) :287-292

[4] Catalytic, asymmetric dimerization of methylketene [J].

Calter, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8006-8007

[5]

Enders D, 2000, SYNLETT, P1371

[6] ENANTIOSELECTIVE ADDITION OF AROMATIC THIOLS TO A KETENE [J].

FEHR, C ;

STEMPF, I ;

GALINDO, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07) :1044-1046

[7] ON ENANTIOMORPH-POLARITY ESTIMATION [J].

FLACK, HD .

ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881

[8] A ONE-POT CONVERSION OF THE PHENYLDIMETHYLSILYL GROUP INTO A HYDROXYL GROUP [J].

FLEMING, I ;

SANDERSON, PEJ .

TETRAHEDRON LETTERS, 1987, 28 (36) :4229-4232

[9] Enantioselective addition of alcohols to ketenes catalyzed by a planar-chiral azaferrocene: Catalytic asymmetric synthesis of arylpropionic acids [J].

Hodous, BL ;

Ruble, JC ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2637-2638

[10] Stereoselective amination, bisamination, and amination/esterification of bis(trimethylsilyl)-1,2-bisketene initiated by chiral amines [J].

Huang, WW ;

Moore, PA ;

Far, AR ;

Tidwell, TT .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (12) :3877-3879