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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 12期

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

页码：2756 / 2760

页数：5

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