THE SYNTHESIS OF E-ENOL ETHERS OF PROTECTED 4-AMINO ALDEHYDES

被引：11

作者：

ARMSTRONG, SK

COLLINGTON, EW

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 / 05期

关键词：

D O I：

10.1039/p19940000515

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compounds, a novel class of protected homoallylic amines, have been synthesised by a short and efficient route. Acrolein acetals were converted by a modified Michaelis-Arbuzov reaction into alpha-alkoxyallyl(diphenyl)phosphine oxides. 1,3-Dipolar cycloaddition to the alkene part of these molecules gave 5-diphenylphosphinoyl-4,5-dihydroisoxazoles, which were reductively cleaved to obtain delta-amino-beta-hydroxy-alpha-alkoxyalkyl (diphenyl)phosphine oxides. After selective protection as the N-acetyl derivatives, stereospecific Wittig-Horner diphenylphosphinic acid elimination gave the title compounds.

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页码：515 / 519

页数：5

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