Selective complexation of 2-hydroxyethyl esters using Lewis acids

被引：10

作者：

Clapham, G ^{[1
]}

Shipman, M ^{[1
]}

机构：

[1] Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 30期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(99)01051-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Competitive Diels-Alder reactions between ethyl acrylate and 2-hydroxyethyl acrylate (1,3-cyclopentadiene, CH2Cl2, 0 degrees C) in the presence of a variety of Lewis acids indicate that selective complexation of the 2-hydroxyethyl ester can be accomplished, most notably using EtAlCl2. Further Diels-Alder reactions using ethyl 2-hydroxyethyl fumarate support these findings. C-13 NMR studies provide direct evidence for the nature of the interactions between 2-hydroxyethyl esters and EtAlCl2. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5639 / 5642

页数：4

共 10 条

[1] STEREOCHEMISTRY OF THE CATALYZED DIELS-ALDER REACTION BETWEEN CYCLOPENTADIENE AND DIMETHYL MONOTHIONOFUMARATE - SOFT VERSUS HARD LEWIS-ACIDS [J].