Thioether-phosphinite and diphosphinite ligands derived from D-xylose for the copper-catalyzed asymmetric 1,4-addition to 2-cyclohexenone

被引：14

作者：

Guimet, E ^{[1
]}

Diéguez, M ^{[1
]}

Ruiz, A ^{[1
]}

Claver, C ^{[1
]}

机构：

[1] Univ Rovira & Virgili, Dept Quim Fis & Inorgan, Tarragona 43007, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 12期

关键词：

D O I：

10.1016/j.tetasy.2005.05.001

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of thioether phosphinite 1-3 and diphosphinite 4 and 5 ligands. derived from inexpensive D-(+)-xylose, were tested for the first time in the Cu-catalyzed asyminetric 1,4-addition to 2-cyclohexenone 6. Good enantioselectivities (up to 72%) and activities [TOF up to > 1225 mol (mol h(-1))] combined with excellent selectivity in the 1,4 product were obtained. Our results show that activity and selectivity (chemo- and enantioselectivity) depend strongly on the type of functional group at the C-5 position of the carbohydrate backbone, the steric properties of the substittlent in the thioether moiety, the catalyst precursor and the alkylating agent. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2161 / 2165

页数：5

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