Reversal in enantioselectivity of tert-butyl versus phenyl-substituted bis(oxazoline)copper(II) catalyzed hetero Diels-Alder and ene reactions.: Crystallographic and mechanistic studies

被引：113

作者：

Evans, DA ^{[1
]}

Johnson, JS ^{[1
]}

Burgey, CS ^{[1
]}

Campos, KR ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 15期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(99)00395-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

X-Ray crystal structures of the Cu [(S,S)-tert-Bu-bis(oxazoline)](H2O)(2)(SbF6)(2) (6), Cu[(S,S)-Ph-bis(oxazoline)](H2O)(2)(SbF6)(2) (7), and Cu [(S,S)-iso-Pr-bis(oxazoline)](H2O)(2)(SbF6)(2) (8) complexes are presented. Implications of the structural details are considered in the context of the opposite enantiofacial biases conferred by complexes Cu[(S,S)-tert-Bu-bis(oxazoline)](X)(2) (1, X = OTf or Sbf(6)) and Cu[(S,S)-Ph-bis(oxazoline)](X)(2) (2) in hetero Diels-Alder and glyoxylate ene reactions. Structural and mechanistic studies suggest that a change in geometry at the metal center is not necessarily responsible for the reversal in enantioselectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2879 / 2882

页数：4

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