Efficient synthesis of 3-methylene-2-pyrrolidinone and highly exoselective Diels-Alder addition to cyclopentadiene

被引：10

作者：

Fotiadu, F

Pardigon, O

Buono, G

Le Corre, M

Hercouët, A

机构：

[1] Ecole Natl Super Synth Proc & Ingn Chim Aix Mars, UMR 6516 Synthese Catalyse & Chiralite, F-13397 Marseille 20, France

[2] Univ Rennes 1, UMR 6510, Organ Synth Lab, F-35042 Rennes, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(98)02542-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new efficient synthesis of 3-methylene 2-pyrrolidinone 1 involving ylide-lactame 6 is reported. Diels-Alder cycloadditions of 1 to cyclopentadiene exhibited very high exoselectivitics, regardless of the experimental conditions. These results confirm the generality of exoselectivity for conformationally restricted s-cis dienophiles and indicate that the dienophile functionality and dipole moment have little influence on its magnitude. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：867 / 870

页数：4

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