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.

引用

页码：7027 / 7030

页数：4

共 9 条

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