Enantioselective synthesis of 2-benzothiazolyl oxiranes

被引：10

作者：

Florio, S

Capriati, V

Russo, V

机构：

[1] Dipartimento Farmaco-Chimico, Università di Bari, 70125 Bari

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 33期

关键词：

D O I：

10.1016/S0040-4039(97)01298-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithiation of 2-(chloroethyl)benzothiazole la gives (benzothiazolylchloroethyl)lithium Ib. The reaction of Ib with ketones in the presence of (-)-sparteine leads to chlorohydrins 2a-c that cyclize to epoxides 3a-c, enantioselectively, the enantiomeric enrichment being dependent upon the solvent, the lithiating agent, the reaction time. The reaction with aldehydes furnishes chlorohydrins 2d-g and then epoxides 3d-g diastereo-and enantioselectively. (C) 1997 Elsevier Science Ltd.

引用

页码：5843 / 5846

页数：4