Stereoselective 1,3-dipolar cycloaddition of a maleate derivative with azomethine ylides derived from α-amino esters:: Synthesis of 3-pyrrolines

被引：6

作者：

Soret, Adrien

Guillot, Regis

Rousseau, Gerard

Blanco, Luis

Deloisy, Sandrine

机构：

[1] Univ Paris Sud, CNRS, Inst Chim Mol & Mat Orsay, Lab Synth Organ & Methodol, F-91405 Orsay, France

[2] Univ Paris Sud, CNRS, ICMMO, Serv Cristallog, F-91405 Orsay, France

来源：

SYNLETT | 2007年 / 08期

关键词：

cycloadditions; amino esters; ylides; diastereoselectivity; retro reactions;

D O I：

10.1055/s-2007-977449

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new preparation of 3-pyrrolines is described by [3+2] cycloadditions of N-metalated azomethine ylides derived from alpha-amino esters with a dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate derivative, followed by retro-Diels-Alder reactions. This two-step sequence appears superior to the direct reaction of ylides with dimethyl acetylenedicarboxylate and should be applicable to solid-phase synthesis.

引用

页码：1284 / 1288

页数：5

共 18 条

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