Short diastereoselective synthesis of cis- and trans-hexahydropyrido[2,1-a]isoindole derivatives

被引：17

作者：

Alsarabi, A ^{[1
]}

Canet, JL ^{[1
]}

Troin, Y ^{[1
]}

机构：

[1] Univ Clermont Ferrand, Lab Chim Heterocycles & Glucides, Ecole Natl Super Chim Clermont Ferrand, EA 987, F-63174 Aubiere, France

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 49期

关键词：

isoindoles; piperidines; stereoselective synthesis; intramolecular; Mannich reaction;

D O I：

10.1016/j.tetlet.2004.10.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and highly stereoselective access to 4,10b-trans or 4,10b-cis hexahydropyido[2,1-a]isoindole derivatives is reported, both requiring an intramolecular Mannich-type reaction as key step. The cis diastereoisomer is obtained in three steps from a 2-alkyl benzaldehyde through the stereoselective formation of it 2,6-cis-disubstituted piperidine, while the trans stereomer is efficiently obtained, in a single step, if a 2-formyl benzoic acid is involved in the Mannich cyclization process. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：9003 / 9006

页数：4

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