ASYMMETRIC NITRONE-VINYL SULFOXIDE CYCLOADDITIONS - A HIGHLY ENANTIOSELECTIVE SYNTHESIS OF (+)-SEDRIDINE

被引：39

作者：

LOUIS, C ^{[1
]}

HOOTELE, C ^{[1
]}

机构：

[1] FREE UNIV BRUSSELS,FAC SCI,DEPT ORGAN CHEM,B-1050 BRUSSELS,BELGIUM

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 09期

关键词：

D O I：

10.1016/0957-4166(95)00287-Y

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Cycloaddition of 2,3,4,5-tetrahydropyridine-1-oxide 1 to (Z)-(R)-vinyl sulfoxides 2a-d proceeds in high yield to give isoxazolidines 3a-d and 4a-d with complete exo selectivity and with 82-98% asymmetric induction. This method provides an efficient synthesis of the enantiomerically pure piperidine alkaloid (+)-sedridine 6a.

引用

页码：2149 / 2152

页数：4

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