New synthesis of 3-arylpyrrolines

被引：15

作者：

Chang, MY ^{[1
]}

Pai, CL

Kung, YH

机构：

[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan

[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 06期

关键词：

3-arylpyrrolines; 4-aryl-1,2,3,6-tetrahydropyridines; m-chloroperoxybenzoic acid; boron trifluoride etherate;

D O I：

10.1016/j.tetlet.2005.12.008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present an easy and straightforward synthesis of 3-arylpyrrolines 4a-g by repeated treatment of 4-aryl-1,2,5,6-tetrahydropyridines 2a-g with in-chloroperoxybenzoic acid (MCPBA) and boron trifluoride etherate (BF3-OEt2). The transformation proceeds via epoxidation, ring contraction, Baeyer-Villiger oxidation and elimination reaction and affords 3-arylpyrrolines 4a-g with 61-70% yield. This facile strategy was also used to synthesize racemic baclofen (6). (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：855 / 859

页数：5

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