Asymmetric allylic oxidation with biarylbisoxazoline-copper(I) catalysis

被引：69
|
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
收藏
页码：5775 / 5780
页数：6
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