Diastereoselective 5-exo-trig radical cyclisation on N-acryloyl-tetrahydro-1,3-oxazines. A novel approach to enantiopure 3-substituted pyrrolidines

被引：17

作者：

Andres, C ^{[1
]}

DuqueSoladana, JP ^{[1
]}

Iglesias, JM ^{[1
]}

Pedrosa, R ^{[1
]}

机构：

[1] UNIV VALLADOLID,FAC CIENCIAS,DEPT QUIM ORGAN,VALLADOLID 47011,SPAIN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(96)02091-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Acryloyl-2-(phenylselenomethyl)-tetrahydro-1,3-oxazine 1 generates a carbon-centred radical in the presence of tri-n-butyltin hydride and AIBN. This radical underwent diastereoselective 5-exo-trig cyclisation leading to a mixture of five-membered lactams 2a and 2b (d.e. 68%). Chromatographic separation of the diastereomers and elimination of the chiral auxiliary provided enantiopure (R)-3-methylpyrrolidine in good chemical yield. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：9085 / 9086

页数：2

共 19 条

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