Asymmetric allylic oxidation with biarylbisoxazoline-copper(I) catalysis

被引：70

作者：

Andrus, MB ^{[1
]}

Asgari, D ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

TETRAHEDRON | 2000年 / 56卷 / 32期

基金：

美国国家科学基金会;

关键词：

allylic oxidation; asymmetric synthesis; cycloalkene; oxidation;

D O I：

10.1016/S0040-4020(00)00425-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Eight new bi-o-tolyl bisoxazolines were made and used as ligands in the copper catalyzed asymmetric allylic oxidation reaction. Three benzoyl tert-butyl peresters, p-nitro, o-iodo, and 2,4,6-trichloro were made and used with cyclohexene and cyclopentene with the ligands complexed to copper(I) hexafluorophosphate (10 mol%). High selectivities (73% ee, 78% yield) were obtained with the nitroperester and la (S,S,S R=Ph) and cyclohexene. For the cyclopentene, 1c (R=Bn) was best at 72% ee, 63% yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5775 / 5780

页数：6

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