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
收藏
页码：4518 / 4521
页数：4
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