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
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.
引用
收藏
页码:5799 / 5802
页数:4
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