A NEW METHOD FOR STEREOSELECTIVE HOMOALLYLIC AMINE SYNTHESIS

被引：42

作者：

ARMSTRONG, SK

COLLINGTON, EW

KNIGHT, JG

NAYLOR, A

WARREN, S

机构：

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

[2] GLAXO GRP RES LTD,WARE SG12 0DP,HERTS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 13期

关键词：

D O I：

10.1039/p19930001433

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrile oxide cycloadditions to readily available allylic diphenylphosphine oxides 2 proceeded regioselectively and stereoselectively to give 5-(1'-diphenylphosphinoylalkyl)isoxazolines 4 and 5. These heterocycles were reduced to delta-amino-beta-hydroxyalkyldiphenylphosphine oxides 6 and 7 using a combination of sodium borohydride and nickel(II) chloride. Stereospecific elimination of diphenylphosphinic acid from the reduction products using sodium hydride in N,N-dimethylformamide gave homoallylic primary amines 8 and 9 of defined stereochemistry.

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页码：1433 / 1447

页数：15

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