Regio- and stereoselective 6-exo-trig radical cyclisations onto chiral perhydro-1,3-benzoxazines:: synthesis of enantiopure 3-alkylpiperidines

被引：26

作者：

Pedrosa, R ^{[1
]}

Andrés, C ^{[1
]}

Duque-Soladana, JP ^{[1
]}

Rosón, CD ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(00)00230-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiopure 3-alkyl substituted piperidines are prepared by diastereoselective 6-exo-trig cyclisation of perhydro-1,3-benzoxazines derived from (-)-(8)-amino menthol. The diastereoselective cyclisation is promoted by tributyltin hydride, and the competitive 1,5-hydrogen migration depends on the position of the acceptor double bond and the radical site. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2809 / 2821

页数：13

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