THE STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED OLEFINS BY THE REACTION OF (2-PHENYLTHIOCYCLOBUTYL)METHYL BENZOATES AND METHYL ETHERS WITH SILYL NUCLEOPHILES

被引：4

作者：

FUJIWARA, T

IWASAKI, T

MIYAGAWA, J

TAKEDA, T

机构：

来源：

CHEMISTRY LETTERS | 1994年 / 02期

关键词：

D O I：

10.1246/cl.1994.343

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Lewis acid-promoted reaction of 2-phenylthiocyclobutanemethanol derivatives with silyl nucleophiles gave the corresponding trisubstituted olefins with high stereoselectivity in good yields. It is suggested that the reaction proceeds via the thionium ion intermediate.

引用

收藏

页码：343 / 346

页数：4

相关论文

共 19 条

[1]

ASTLES PC, COMPREHENSIVE ORGANI, V6, P1016

[2]

CAUBERE P, COMPREHENSIVE ORGANI, V8, P835

[3] THIOSILANES, A PROMISING CLASS OF REAGENTS FOR SELECTIVE CARBONYL PROTECTION [J].

EVANS, DA ;

TRUESDALE, LK ;

GRIMM, KG ;

NESBITT, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (15) :5009-5017

[4] THE METHOXYCARBONYLALKYLATION AND METHOXYCARBONYLALKYLIDENATION OF SILYL ENOL ETHERS [J].

FLEMING, I ;

IQBAL, J .

TETRAHEDRON LETTERS, 1983, 24 (03) :327-328

[5] STEREOSELECTIVE SYNTHESIS OF (E)-GAMMA,DELTA-UNSATURATED, AND (Z)GAMMA,DELTA-UNSATURATED KETONES USING TRANS-2-PHENYLTHIOCYCLOBUTYL KETONES [J].

FUJIWARA, T ;

IWASAKI, T ;

TAKEDA, T .

CHEMISTRY LETTERS, 1993, (08) :1321-1324

[6] ALKYLATION OF ENOL SILYL ETHERS WITH VINYLTHIONIUM IONS GENERATED FROM 1,1-BIS(PHENYLTHIO)PROPENES AND 1,3-BIS(PHENYLTHIO)PROPENES [J].

HUNTER, R ;

MICHAEL, JP ;

WALTER, DS .

TETRAHEDRON LETTERS, 1992, 33 (37) :5413-5416

[7] CARBON CARBON BOND FORMING REACTIONS VIA ALPHA-PHOSPHORYL-ALPHA-THIO CARBOCATIONS [J].

ISHIBASHI, H ;

SATO, T ;

IRIE, M ;

ITO, M ;

IKEDA, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (05) :1095-1098

[8]

KRIEF A, 1991, COMPREHENSIVE ORGANI, V3, P85

[9] A REGIOSPECIFIC SYNTHESIS OF GAMMA-KETO ESTERS - THE ALKYLATION OF O-SILYLATED ENOLATES WITH METHYL ALPHA-CHLORO-PHENYLTHIOACETATE ALPHA-PHENYLTHIOACETATE [J].

LEE, TV ;

OKONKWO, JO .

TETRAHEDRON LETTERS, 1983, 24 (03) :323-326

[10] ACYCLIC STEREOSELECTION - HIGH DIASTEREOFACIAL SELECTIVITY IN NUCLEOPHILIC ADDITIONS TO CHIRAL THIONIUM IONS [J].

MORI, I ;

BARTLETT, PA ;

HEATHCOCK, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7199-7200