COMPLEXES CONTAINING A LEWIS-ACID AND BRONSTED ACID FOR THE CATALYTIC ASYMMETRIC DIELS-ALDER REACTION

被引：29
|
作者：
AGGARWAL, VK [1 ]
ANDERSON, E [1 ]
GILES, R [1 ]
ZAPARUCHA, A [1 ]
机构：
[1] SMITHKLINE BEECHAM,TONBRIDGE TN11 9AN,KENT,ENGLAND
来源：
TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 06期
基金：
英国工程与自然科学研究理事会;
关键词：
D O I：
10.1016/0957-4166(95)00163-J
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Complexes containing a Lewis acid and a Bronsted acid have been prepared by the reaction of an amino alcohol and a trihaloborane. The structures of the complexes were determined by B-11, H-1, and C-13 analysis and shown to be the acyclic structures 5 rather than the possible cyclic structures 6 which only contain the single Lewis acid. A variety of amino alcohols were combined with BBr3 and BCl3 and tested in Diels Alder reactions between methacrolein and cyclopentadiene. Whilst very high exo selectivity was observed, enantioselectivity was variable depending on the amino alcohol used, Prolinol 4 gave the highest ee (97%) but quinidine gave the highest ee (64%) for a naturally occurring amino alcohol.
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收藏
页码：1301 / 1306
页数：6
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