1,3-DIPOLAR CYCLOADDITION OF ENANTIOPURE GAMMA-OXYGENATED-ALPHA,BETA-UNSATURATED PHENYL SULFONES WITH NITRILE OXIDES

被引：16
|
作者：
DEBLAS, J [1 ]
CARRETERO, JC [1 ]
DOMINGUEZ, E [1 ]
机构：
[1] UNIV AUTONOMA MADRID,FAC CIENCIAS,DEPT QUIM ORGAN CI,E-28049 MADRID,SPAIN
来源：
TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 05期
关键词：
D O I：
10.1016/0957-4166(95)00118-9
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The 1,3-dipolar cycloadditions of several enantiopure gamma-oxygenated-alpha,beta-unsaturated : sulfones with acetonitrile and benzonitrile oxides have been studied. The reactions occurred at room temperature with moderate yields (31-65%), complete regioselectivity in favour of the isoxazolines with the phenylsulfonyl group at C-4, and moderate or high anti-stereoselectivity. After reductive elimination of the sulfonyl group and further reduction of N-O bond, enantiomerically pure beta-hydroxyketones or 1,3-aminoalcohols were obtained.
引用
收藏
页码：1035 / 1038
页数：4
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