A Palladium-Catalyzed Formal (4+1) Annulation: A New Approach to Cyclopentene Construction

被引：18
|
作者：
Widenhoefer, Ross A. [1 ]
机构：
[1] Duke Univ, Dept Chem, Durham, NC 27708 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 38期
关键词：
annulation; cycloaddition; cyclopentenes; homogeneous catalysis; palladium; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; HIGHLY SUBSTITUTED CYCLOPENTENONES; BETA-KETO-ESTERS; STEREOSELECTIVE-SYNTHESIS; CYCLOADDITION; REARRANGEMENT; CYCLIZATION; ROUTE;
D O I：
10.1002/anie.200902404
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Juggling rings: A novel two-step procedure achieves the formal (4+1) annulation of a conjugated diene with a β-keto ester to form a functionalized cyclopentene in good yield under mild conditions. The transformation involves a palladium-catalyzed intramolecular oxidative cyclopropanation of an ε-dienyl β-keto ester followed by magnesium iodide mediated rearrangement of the resulting vinyl cyclopropane. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：6950 / 6952
页数：3
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