Lewis acid-catalysed rearrangement/reduction of 1-phenyloxiranemethanamines: Synthesis of beta-phenethylamines

被引：12

作者：

Harden, RC

Hodgkinson, TJ

McKillop, A

Prowse, WG

Urquhart, MWJ

机构：

[1] UNIV E ANGLIA,SCH CHEM SCI,NORWICH NR4 7TJ,NORFOLK,ENGLAND

[2] LILLY RES CTR LTD,WINDLESHAM GU20 6PH,SURREY,ENGLAND

来源：

TETRAHEDRON | 1997年 / 53卷 / 01期

关键词：

D O I：

10.1016/S0040-4020(96)00974-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of 1-phenyloxiranemethanamines has been prepared and their reactions with sodium cyanoborohydride under boron trifluoride catalysis have been investigated. In general the products were the corresponding 2-amino-3-phenylpropan-1-ols derived from Lewis acid-mediated ring opening of the epoxide in an aza-Payne manner and benzylic reduction of the intermediate aziridinium species. Copyright (C) 1996 Elsevier Science Ltd

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页码：21 / 36

页数：16

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