BIS(IMINE)-COPPER(II) COMPLEXES AS CHIRAL LEWIS-ACID CATALYSTS FOR THE DIELS-ALDER REACTION

被引：113
作者：
EVANS, DA
LECTKA, T
MILLER, SJ
机构：
[1] Department of Chemistry, Harvard University, Cambridge
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 44期
关键词：
D O I：
10.1016/S0040-4039(00)61588-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report the Diels-Alder reactions of imide-derived dienophiles 2a-2d and 4b-4d with cyclopentadiene catalyzed by square-planar Cu(OTf)2-bis(imine) complexes. The 2,6-dichlorophenyl-substituted ligand la was found to be generally the most effective for a range of substrates, affording products from 83-94% enantiomeric excess. Although endo:exo diastereoselectivity for the oxo-substituted imides 2a-2d is low, significant improvement is achieved with the thiazolidine-2-thione analogues 4b-4d, which provide enhanced dienophile reactivity and enhanced endo:exo diastereoselection.
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页码：7027 / 7030
页数：4
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