Enantioselective radical-chain hydrosilylation of prochiral alkenes using optically active thiol catalysts

被引：57

作者：

Haque, MB ^{[1
]}

Roberts, BP ^{[1
]}

机构：

[1] UNIV LONDON UNIV COLL,DEPT CHEM,CHRISTOPHER INGOLD LABS,LONDON WC1H 0AJ,ENGLAND

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(96)90165-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The radical-chain hydrosilylation of alkenes of the type H2C=CR(1)R(2), catalysed by small amounts of optically active thiols, affords functionalised organosilanes in moderate enantiomeric purity by a mechanism which involves enantioselective hydrogen-atom transfer from the thiol to a prochiral beta-silylalkyl radical. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：9123 / 9126

页数：4

共 13 条

[1] ASYMMETRIC EPOXIDATION USING CHIRAL SULFUR YLIDES [J].

AGGARWAL, VK ;

KALOMIRI, M ;

THOMAS, AP .

TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :723-730

[2] THIOLS AS POLARITY REVERSAL CATALYSTS FOR HYDROGEN-ATOM TRANSFER FROM ORGANOSILANES TO ALKYL RADICALS - REDUCTION OF ALKYL-HALIDES BY TRIETHYLSILANE [J].

ALLEN, RP ;

ROBERTS, BP ;

WILLIS, CR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (18) :1387-1388

[3] RADICAL CHAIN REDUCTION OF ALKYL-HALIDES, DIALKYL SULFIDES AND O-ALKYL S-METHYL DITHIOCARBONATES TO ALKANES BY TRIALKYLSILANES [J].

COLE, SJ ;

KIRWAN, JN ;

ROBERTS, BP ;

WILLIS, CR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :103-112

[4] ENANTIOSELECTIVE HYDROGEN-ATOM ABSTRACTION BY HOMOCHIRAL SILANETHIYL RADICALS [J].

DANG, HS ;

ROBERTS, BP .

TETRAHEDRON LETTERS, 1995, 36 (21) :3731-3734

[5] POLARITY-REVERSAL CATALYSIS BY THIOLS OF RADICAL-CHAIN HYDROSILYLATION OF ALKENES [J].

DANG, HS ;

ROBERTS, BP .

TETRAHEDRON LETTERS, 1995, 36 (16) :2875-2878

[6]

KIETER H, 1966, TETRAHEDRON LETT, P6163

[7] DEOXYGENATION OF ALCOHOLS BY THE REACTIONS OF THEIR XANTHATE ESTERS WITH TRIETHYLSILANE - AN ALTERNATIVE TO TRIBUTYLTIN HYDRIDE IN THE BARTON-MCCOMBIE REACTION [J].

KIRWAN, JN ;

ROBERTS, BP ;

WILLIS, CR .

TETRAHEDRON LETTERS, 1990, 31 (35) :5093-5096

[8] PREPARATION OF OPTICALLY-ACTIVE NEW MERCAPTO CHIRAL AUXILIARIES DERIVED FROM CAMPHOR [J].

LEE, DS ;

HUNG, SM ;

LAI, MC ;

CHU, HY ;

YANG, TK .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1993, 25 (06) :673-679

[9]

LEVINA RY, 1956, DOKL AKAD NAUK, V106, P51

[10]

MENDENHALL GD, 1983, TETRAHEDRON LETT, V24, P451

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