ON THE STEREOSELECTIVITY OF NITRONE ADDITION TO ALPHA-DIPHENYLPHOSPHINOYLALKENES

被引：8

作者：

ARMSTRONG, SK

COLLINGTON, EW

STONEHOUSE, J

WARREN, S

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND

[2] GLAXO GRP RES LTD,GREENFORD UB6 0HE,MIDDX,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 19期

关键词：

D O I：

10.1039/p19940002825

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title reaction was investigated for both achiral and alpha-chiral alkenes 1-3, and for cyclic and acyclic nitrones 4 and 8. In each case, addition to allyldiphenyl phosphine oxide 1 gave a single isoxazolidine product. The configurations of these isoxazolidines (5 and 9) were investigated by NMR methods, and found to be consistent with reaction via exo transition states. Nitrone additions to alpha-chiral alpha-diphenylphosphinoyl alkenes 2 and 3 gave two diastereoisomeric products in all cases studied. The configurations of these isoxazolidines (6, 7,10, 11) were assigned by analogy with the archiral cases, and also by analogy with the addition of nitrile oxides to the same alkenes. In one case (6a) this was confirmed by chemical conversion. This conversion also demonstrated the potential of this method for the synthesis of 2-(alk-2'-enyl)piperidines, e.g. 17, having defined double-bond geometry.

引用

页码：2825 / 2831

页数：7

共 18 条

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