Chiral C2-symmetric CuII complexes as catalysts for enantioselective hetero-Diels-Alder reactions

被引：0

作者：

Evans, DA ^{[1
]}

Olhava, EJ ^{[1
]}

Johnson, JS ^{[1
]}

Janey, JM ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 1998年 / 37卷 / 24期

关键词：

asymmetric catalysis; copper; cycloadditions; Lewis acids; synthetic methods;

D O I：

10.1002/(SICI)1521-3773(19981231)37:24<3372::AID-ANIE3372>3.0.CO;2-K

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Air-stable and recyclable, the Cu(II)- (bis)oxazoline complex 1 efficiently catalyzes diastereo- and enantioselective hetero-Diels-Alder reactions between β,γ-unsaturated α-keto acid derivatives 2 and vinyl ethers for the synthesis of substituted dihydropyrans 3 [Eq. (1)]. Results of the crystal structure analysis of 1 in combination with calculations on model compounds indicate the formation of a reactive intermediate through replacement of the two H2O ligands with a chelating substrate. X = OEt, N(OMe)Me; R = alkyl, aryl, alkoxy, thiobenzyl.

引用

页码：3372 / 3375

页数：4

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