Ring-Contraction Strategy for the Practical, Scalable, Catalytic Asymmetric Synthesis of Versatile γ-Quaternary Acylcyclopentenes

被引:50
作者
Hong, Allen Y. [1 ]
Krout, Michael R. [1 ]
Jensen, Thomas [1 ]
Bennett, Nathan B. [1 ]
Harned, Andrew M. [1 ]
Stoltz, Brian M. [1 ]
机构
[1] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, Div Chem & Chem Engn, Pasadena, CA 91125 USA
关键词
aldol reaction; allylation; asymmetric catalysis; rearrangement reactions; ring contraction; ALLYLIC ALKYLATION; BETA-KETOESTERS; ENOL ETHERS; SESQUITERPENOIDS;
D O I
10.1002/anie.201007814
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Contraction action! A simple protocol for the catalytic asymmetric synthesis of highly functionalized γ-quaternary acylcyclopentenes (see schematic) in up to 91 % overall yield and 92 % ee has been developed. The reaction sequence employs a palladium-catalyzed enantioselective alkylation reaction and exploits the unusual stability of β-hydroxy cycloheptanones to achieve a general and robust method for performing two-carbon ring contractions. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2756 / 2760
页数:5
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