Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects

被引：275

作者：

Arnold, LA ^{[1
]}

Imbos, R ^{[1
]}

Mandoli, A ^{[1
]}

de Vries, AHM ^{[1
]}

Naasz, R ^{[1
]}

Feringa, BL ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

来源：

TETRAHEDRON | 2000年 / 56卷 / 18期

关键词：

phosphoramidite ligand; copper; enantioselective conjugate addition; enones; non-linear effect; diethyl zinc; catalytic 1,4-addition;

D O I：

10.1016/S0040-4020(00)00142-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of new chiral phosphoramidites was synthesised and tested in the copper-catalysed enantioselective conjugate addition of diethylzinc to cyclohexenone and chalcone in order to assess the structural features that are important for stereocontrol. A sterically demanding amine moiety is essential to reach high e.e.'s. Enantioselectivities for chalcones up to 89% and for cyclic enones up to 98% were found. Studies on non-linear effects with the best ligands for both cyclohexenone and chalcone showed clear non-linear effects for both cyclic and acyclic enones. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2865 / 2878

页数：14

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