SYNTHESIS OF ASYMMETRIC (E)-ALPHA-[2-PHENYL(ETHYL)CYCLOPROPYL]GLYCINES FROM SERINE BY DIASTEREOSELECTIVE DIBROMOCYCLOPROPANATION

被引：7

作者：

DEFRUTOS, MP ^{[1
]}

FERNANDEZ, MD ^{[1
]}

FERNANDEZALVAREZ, E ^{[1
]}

BERNABE, M ^{[1
]}

机构：

[1] CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN

来源：

TETRAHEDRON | 1992年 / 48卷 / 06期

关键词：

D O I：

10.1016/S0040-4020(01)88208-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthesis of (E)-alpha-(2-phenylcyclopropyl)glycines and also of a homolog of allocoronamic acid, namely (E)-alpha-(2-ethylcyclopropyl)glycine, is reported. The key step is the dibromocyclopropanation of tert-butyl (E, 4R)- or (E, 4S)-2,2-dimethyl-4-(2'-phenylvinyl)- and -(2'-ethylvinyl)-3-oxazolidinecarboxylates, easily prepared from L- or D-serine. This reaction gives good diastereomeric ratios of dibromocyclopropanes. The major compounds were transformed, in three steps, in the corresponding cyclopropylaminoacids.

引用

页码：1123 / 1130

页数：8

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