TARTROL-derived chiral phosphine-phosphite ligands and their performance in enantioselective Cu-catalyzed 1,4-addition reactions

被引：14

作者：

Dindaroglu, Mehmet ^{[1
]}

Akyol, Sema ^{[1
]}

Simsir, Hamza ^{[1
]}

Neudoerfl, Joerg-Martin ^{[1
]}

Burke, Anthony ^{[2
,3
]}

Schmalz, Hans-Guenther ^{[1
]}

机构：

[1] Univ Cologne, Dept Chem, D-50939 Cologne, Germany

[2] Univ Evora, Dept Chem, P-597000 Evora, Portugal

[3] Univ Evora, Ctr Quim Evora, P-597000 Evora, Portugal

来源：

TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 11期

关键词：

GRIGNARD-REAGENTS;

D O I：

10.1016/j.tetasy.2013.04.008

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

By using (R,R,R,R)-2,3-dimethoxy-2,3-dimethyl-1,4-dioxane-5,6-bis-diphenylmethanol (TARTROL) as a chiral building block, a set of six modular phosphine-phosphite ligands (with a 1,2-phenylene backbone) were synthesized and evaluated in the Cu-catalyzed asymmetric 1,4-addition of Grignard reagents to cyclohexenone. Ligands with bulky substituents at the ortho- and para-positions to the chiral phosphite moiety were found to be the most selective affording the 1,4-addition products with enantioselectivities of up to 84% ee. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：657 / 662

页数：6

共 35 条

[1] Gaining Absolute Control of the Regiochemistry in the Cobalt-Catalyzed 1,4-Hydrovinylation Reaction [J].