Selective Lewis acid complexation of 2-hydroxyethyl esters using competitive Diels-Alder reactions as a mechanistic probe

被引：9

作者：

Clapham, G ^{[1
]}

Shipman, M ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2000年 / 56卷 / 08期

基金：

英国工程与自然科学研究理事会;

关键词：

Diels-Alder reactions; EtAlCl2; (2R*; 3R*)-2-(3-hydroxy)butyl acrylate; 2-hydroxyethyl esters; selective Lewis acid complexation;

D O I：

10.1016/S0040-4020(99)01071-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Competitive Diels-Alder reactions involving ethyl acrylate, 2-hydroxyethyl acrylate and 2-methoxyethyl acrylate indicate that certain Lewis acids (e.g. EtAlCl2) selectively complex to the 2-hydroxyethyl ester group. Studies using ethyl 2-hydroxyethyl fumarate support these findings. C-13 NMR spectroscopy provides some evidence regarding the nature of the interactions between 2-hydroxyethyl esters and EtAlCl2. The influence of EtAlCl2 on the level of diastereocontrol observed in the Diels-Alder reactions of (2R*,3R*)-2(3-hydroxy)butyl acrylate is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：1127 / 1134

页数：8

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