(S)-ethyl 4,4-dimethyl pyroglutamate as a new 'quat' chiral auxiliary in aldol condensations

被引：9

作者：

Ezquerra, J ^{[1
]}

Rubio, A ^{[1
]}

Martin, J ^{[1
]}

Navio, JLG ^{[1
]}

机构：

[1] UNIV ALCALA DE HENARES, DEPT QUIM ORGAN, ALCALA DE HENARES 28871, MADRID, SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(97)00028-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enolates I, derived from the N-propionyl derivative of the 'quat' chiral auxiliary (S)-ethyl 4,4-dimethyl pyroglutamate 4 undergo highly stereoselective aldol reactions, which upon hydrolysis and removal of the chiral auxiliary yields the (2R,3R)-3-hydroxy-2-methylpropionic acid 9 in homochiral form. Remarkably, the stereogenic center of 4 was not affected during all the chemical transformations and it could be regenerated after the process in 70% yield. (C) 1997 Elsevier Science Ltd.

引用

页码：669 / 671

页数：3

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