Stereoisomerically Pure Trisubstituted Vinylaluminum Reagents and their Utility in Copper-Catalyzed Enantioselective Synthesis of 1,4-Dienes Containing Z or E Alkenes

被引：115

作者：

Akiyama, Katsuhiro ^{[1
]}

Gao, Fang ^{[1
]}

Hoveyda, Amir H. ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 02期

关键词：

allylic alkylation; enantioselective catalysis; hydroalumination; N-heterocyclic carbenes; vinylaluminum reagents; N-HETEROCYCLIC CARBENES; ASYMMETRIC 1,4-ADDITION; ALLYLIC ALKYLATION; ORGANOMETALLIC COMPOUNDS; ALKYNES; ADDITIONS; HYDROSILYLATION; HYDRALUMINATION; VINYLATION; METATHESIS;

D O I：

10.1002/anie.200905223

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

"Chemical Equation Presented" The desired isomer of a chiral 1,4-diene containing an E or Z double bond can be accessed readily by a regio- and stereoselective hydroalumination of silyl-substituted alkynes and subsequent enantioselective copper-catalyzed allylic alkylation. The utility of the procedure was demonstrated through the synthesis of (-)-nyasol (see scheme). dibal-H=diisobutylaluminum hydride, NHC=N-heterocyclic carbene. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：419 / 423

页数：5

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