Catalytic and asymmetric [2,3]sigmatropic rearrangement:: Co(III)-salen catalyzed S-ylide formation from allyl aryl sulfides and their rearrangement

被引：57

作者：

Fukuda, T ^{[1
]}

Irie, R ^{[1
]}

Katsuki, T ^{[1
]}

机构：

[1] Kyushu Univ 33, Grad Sch Sci, Dept Mol Chem, Higashi Ku, Fukuoka 8128581, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 03期

关键词：

D O I：

10.1016/S0040-4020(98)01065-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of allyl aryl sulfides and a-diazoacetic acid esters in the presence of optically active Co(III)-salen complex (8-Br) provided 3-substituted 2-arylthio-4-pentenoic acid esters stereoselectively py way of enantioselective S-ylide formation and subsequent diastereoselective [2,3]sigmatropic rearrangement. For example, the reaction of cinnamyl phenyl sulfide and (-)-menthyl alpha-diazoacetate provided (-)-menthyl (2R,3S)-2-phenylthio-3-phenyl-4-pentenoate of 74% de preferentially. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：649 / 664

页数：16

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