SYNTHESIS OF (R)-2,3-METHANOVALINE AND (S)-2,3-METHANOVALINE FROM (2S)-N-BENZOYL-2-TERT-BUTYL-4-METHYLENE-1,3-OXAZOLIDIN-5-ONE

被引：26

作者：

CHINCHILLA, R

NAJERA, C

GARCIAGRANDA, S

MENENDEZVELAZQUEZ, A

机构：

[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,APDO 99,E-03080 ALICANTE,SPAIN

[2] UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33006 OVIEDO,SPAIN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(00)73864-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of (2S)-N-benzo) 2-tert-butyl-4-methylene-1,3-oxazolidin-5 one (9) with isopropylidene-triphenylphosphorane at room temperature gives the corresponding cis and trans spirocyclopropane derivatives 10 in ca. 1:1 ratio. After separation of both diastereomers, by recrystallization and flash chromatography, and further acid hydrolysis, enantiomerically pure (R)- and (S)-2,3-methanovaline 11 are obtained.

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页码：5799 / 5802

页数：4

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