Naphthyl-substituted bisoxazoline and pyridylbisoxazoline-copper(I) catalysts for asymmetric allylic oxidation

被引：25

作者：

Zhou, Ziniu ^{[1
,2
]}

Andrus, Merritt B. ^{[1
]}

机构：

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

[2] Zhejiang Pharmaceut Coll, Yinxian Ave Eastern Sect 888, Ningbo 315100, Zhejiang, Peoples R China

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 34期

基金：

美国国家科学基金会;

关键词：

Allylic oxidation; Bisoxazoline-copper(I) complex; Naphthyl; COPPER(I) COMPLEXES; KHARASCH REACTION; TERMINAL OLEFINS; EFFICIENT; LIGAND; ACYLOXYLATION; STRATEGY; ESTERS; BIS(OXAZOLINE); ALKENES;

D O I：

10.1016/j.tetlet.2012.06.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of naphthyl substituted malonyl-derived and pyridine-based bisoxazolines and their applications in the asymmetric allylic oxidation of cyclohexene with t-butyl p-nitroperbenzoate have been performed with much improved reactivity (75% yield) while maintaining very good enantioselectivity (85% ee). A 1-naphthyl group as the side chain of the oxazoline ligand was found to be optimal. Correlations between the nature of the substituents on the bisoxazolines and the reactivity/selectivity have been established. Tridentate pyridylbisoxazoline ligands with naphthyl groups were also synthesized and employed. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：4518 / 4521

页数：4

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