The use of the aza-Diels-Alder reaction in the synthesis of pinidine and other piperidine alkaloids

被引：14

作者：

Bailey, PD ^{[1
]}

Smith, PD ^{[1
]}

Morgan, KM ^{[1
]}

Rosair, GM ^{[1
]}

机构：

[1] Heriot Watt Univ, Dept Chem, Edinburgh EH14 4AS, Midlothian, Scotland

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 06期

关键词：

alkaloids; Diels-Alder reaction; piperidines;

D O I：

10.1016/S0040-4039(01)02149-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The imine Ph2CHN-CHCO2Et, generated from benzhydrylamine and ethyl glyoxylate. provides a Diets-Alder adduct with 1,3-pentadiene from which a range of cis-2,6-disubstituted piperidines can be accessed; the benzhydryl group confers high diastereocontrol for derivatising the six- membered ring, allowing access to 2,5,6-trisubstituted piperidines. and to 2,6-disubstituted piperidines such as pinidine. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1071 / 1074

页数：4

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