X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .32. GENERATION OF NITRONES FROM OXIMES - TANDEM MICHAEL ADDITION-1,3-DIPOLAR CYCLOADDITION REACTIONS - BACKGROUND AND CLASS-1 PROCESSES

被引：35

作者：

GRIGG, R ^{[1
]}

HEANEY, F ^{[1
]}

SURENDRAKUMAR, S ^{[1
]}

WARNOCK, WJ ^{[1
]}

机构：

[1] QUEENS UNIV BELFAST,DEPT CHEM,BELFAST BT9 5AG,ANTRIM,NORTH IRELAND

来源：

TETRAHEDRON | 1991年 / 47卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(01)87116-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intermolecular Michael addition of aldoximes and ketoximes to electronegative olefins generates nitrones. The keto nitrones can be trapped in regiospecific intermolecular cycloaddition reactions giving single cycloadducts in good yield. Chemospecific 1:1:1 cycloadducts are obtained from ketoximes, monosubstituted electronegative olefins (Michael acceptor) and N-methylmaleimide (dipolarophile), whilst the chemoselectivity of the corresponding reactions with aldoximes is dependent on the oxime stereochemistry. Z-Aldoximes show high chemospecificity whilst E-aldoximes are much less chemoselective.

引用

页码：4477 / 4494

页数：18

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