Formation of Quaternary Chiral Centers by N-Heterocyclic Carbene-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Trisubstituted Cyclic Enones

被引：94

作者：

Kehrli, Stefan ^{[1
]}

Martin, David ^{[2
]}

Rix, Diane ^{[3
]}

Mauduit, Marc ^{[3
]}

Alexakis, Alexandre ^{[1
]}

机构：

[1] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland

[2] UPCAM iSm2 Serv A62, F-3397 Marseille 20, France

[3] Ecole Natl Super Chim Rennes, F-35700 Rennes, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 32期

基金：

新加坡国家研究基金会;

关键词：

asymmetry; conjugate addition; copper; Grignard reaction; N-heterocyclic carbenes; RING-CLOSING METATHESIS; ARYL ALUMINUM REAGENTS; STEREOGENIC CENTERS; ALLYLIC SUBSTITUTION; ENANTIOSELECTIVE SYNTHESIS; DIALKYLZINC REAGENTS; NHC LIGANDS; PHOSPHORAMIDITE LIGAND; UNSATURATED ESTERS; MELDRUMS ACIDS;

D O I：

10.1002/chem.201000471

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The copper-catalyzed conjugate addition of Grignard reagents to 3-substituted cyclic enones allows the formation of all-carbon chiral quaternary centers We demonstrate in this article that N-heterocyclic carbencs act as efficient chiral ligands for this transformation High enantioselectivities (up to 96% ee) could be obtained for a variety of substrates

引用

页码：9890 / 9904

页数：15

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