A practical method for enantioselective synthesis of all-carbon quaternary stereogenic centers through NHC-Cu-catalyzed conjugate additions of alkyl- and arylzinc reagents to β-substituted cyclic enones

被引：198

作者：

Lee, Kang-Sang ^{[1
]}

Brown, M. Kevin ^{[1
]}

Hird, Alexander W. ^{[1
]}

Hoveyda, Amir H. ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 22期

关键词：

D O I：

10.1021/ja062061o

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present the first examples of Cu-catalyzed enantioselective conjugate additions of alkyl- and arylzinc reagents to unactivated cyclic β-substituted enones. Transformations are promoted in the presence of 2.5-15 mol % of a readily available chiral NHC-based Cu complex, affording the desired products bearing all-carbon quaternary stereogenic centers in 67→98% yield and in up to 97% ee. Catalytic enantioselective reactions can be carried out on a benchtop, with undistilled solvent and commercially available (not further purified) Cu salts. Mechanistic models, accounting for the observed levels and trends in enantioselectivity are provided. Copyright © 2006 American Chemical Society.

引用

页码：7182 / 7184

页数：3

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