[3+2] CYCLOADDITION OF CHIRAL AZOMETHINE YLIDES FROM AMINOSUGAR N-OXIDES - ENANTIOSELECTIVE SYNTHESIS OF 3,4-DISUBSTITUTED PYRROLIDINES

被引：0
|
作者：
CHASTANET, J
FATHALLAH, H
NEGRON, G
ROUSSI, G
机构：
来源：
HETEROCYCLES | 1992年 / 34卷 / 08期
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D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The base deprotonation method, applied to amino-sugar N-oxides prepared from methyl 2,3-anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside (8) and methyl 2,3-anhydro-4,6-O-benzylidene-alpha-D-allopyranoside (9), allows the easy generation of complex and very reactive sugar azomethine ylides. Fair yields of the major diastereomeric pyrrolidines resulting from [3+2] cycloaddition to stilbene are thus obtained with good asymmetric induction. The easy elimination of the chiral appendage as starting epoxides gives access to the enantiomerically enriched 3,4-diphenylpyrrolidines.
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页码：1565 / 1572
页数：8
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