Bidentate NHC-based chiral ligands for efficient Cu-catalyzed enantioselective allylic alkylations: Structure and activity of an air-stable chiral Cu complex

被引：230

作者：

Larsen, AO ^{[1
]}

Leu, W ^{[1
]}

Oberhuber, CN ^{[1
]}

Campbell, JE ^{[1
]}

Hoveyda, AH ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 36期

关键词：

D O I：

10.1021/ja046245j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cu-catalyzed addition of alkylzinc reagents to a range of allylic phosphates is promoted efficiently and with high enantioselectivity to afford tertiary as well as quaternary carbon centers (up to 98% ee). Reactions proceed to completion with 0.5-5 mol % catalyst loading and are best promoted by commercially available CuCl2·2H2O. The X-ray structure of the chiral NHC-Ag(I) complex used in the study as well as that of a catalytically active NHC-Cu(II) complex are also reported; both complexes are air-stable and are formed in ≥95% isolated yield. The isolated Cu complex, which can be handled in air, is catalytically active. The present report provides the first precedent for efficient Cu-catalyzed allylic alkylations with chiral NHC ligands. Copyright © 2003 American Chemical Society.

引用

页码：11130 / 11131

页数：2

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