Synthesis of enantioenriched 4-thiazolidinone (-)-LY213829 by chemoselective benzylamide cleavage in the presence of a C-S bond

被引：16

作者：

Hansen, MM

Harkness, AR

Khau, VV

Martinelli, MJ

Deeter, JB

机构：

[1] Chem. Proc. Res./Devmt. Division, Lilly Research Laboratories, Division of Eli Lilly and Company, Indianapolis

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 09期

关键词：

D O I：

10.1016/0957-4166(96)00321-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(R)-2-Methylbenzylamine has been used to covalently ''resolve'' thiol acid 7 and assemble 4-thiazolidinone 8a in one step. Selective deprotection of the 2-methylbenzylamide using lithium in ammonia/THF has been achieved in the presence of a readily hydrogenolyzed C-S bond. Enantioenriched (-)-LY213829 (1) of 98% ee has been prepared by this five step route in 25% yield from aldehyde 2. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：2515 / 2518

页数：4

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