Functionalization of BINOL and application in the homo- and heterogeneous enantioselective epoxidation of α,β-unsaturated ketones

被引：3

作者：

El Kadiri, Moulay Youness ^{[1
]}

Framery, Eric ^{[1
]}

Andrioletti, Bruno ^{[1
]}

机构：

[1] Univ Lyon 1, UMR CNRS 5246, Inst Chim & Biochim Mol & Supramol, Equipe CASYEN, F-69622 Villeurbanne, France

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 47期

关键词：

Enantioselective epoxidation; BINOL; Lanthanide; Homogeneous catalysis; Heterogenous catalysis; CATALYTIC ASYMMETRIC EPOXIDATION; CARBOXYLIC-ACID IMIDAZOLIDES; SUZUKI-MIYAURA REACTIONS; CHIRAL LANTHANUM; UNFUNCTIONALIZED OLEFINS; ALPHA; BETA-EPOXY ESTERS; EFFICIENT SYNTHESIS; UNIQUE REACTIVITY; ALLYLIC ALCOHOLS; AMMONIUM-SALTS;

D O I：

10.1016/j.tetlet.2012.09.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selective functionalization of BINOL derivatives with 3-(dimethylamino)prop-1-yn-1 -yl is described. The corresponding La and Yb complexes were evaluated toward the epoxidation of alpha,beta-unsaturated ketones. The Yb-complexes display the highest catalytic activity and selectivity, affording the expected chiral epoxides in quantitative yields and up to 90% ee in homogeneous conditions, and 93% ee when supported on silica gel. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：6335 / 6338

页数：4

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