DIASTEREOSELECTIVE SYNTHESIS OF SUBSTITUTED GLUTAMIC-ACID DERIVATIVES VIA MICHAEL ADDITIONS OF N-[BIS(METHYLTHIO)METHYLENE]GLYCINATES UNDER SOLID-LIQUID PHASE-TRANSFER CATALYSIS

被引：24
作者：
ALVAREZIBARRA, C
CSAKY, AG
MAROTO, M
QUIROGA, ML
机构：
[1] Departamento de Quimica Orgánica I, Facultad de Quimica, Universidad Complutense
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 21期
关键词：
D O I：
10.1021/jo00126a020
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Michael additions of the enolates of ethyl and tert-butyl N-[bis(methylthio)methylene]glycinates with alpha,beta-unsaturated esters and ketones under solid-liquid phase transfer catalysis allowed for the highly diastereoselective synthesis of substituted glutamic acid derivatives through a transition state chelation-controlled by the catalyst with a like approach of reactants. Selective removal of the iminodithiocarbonate protecting group with concomitant cyclization gave rise to 3-substituted pyroglutamates and 1,3,4-trisubstitued Delta(1)-pyrrolines with retention of configuration.
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收藏
页码：6700 / 6705
页数：6
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