Palladium-Catalyzed Asymmetric Allylic Alkylation of 2-Acylimidazoles as Ester Enolate Equivalents

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• 作者：Barry M. Trost ; Konrad Lehr ; David J. Michaelis ; Jiayi Xu ; Andreas K. Buckl
• 刊名：Journal of the American Chemical Society
• 出版年：2010
• 出版时间：July 7, 2010
• 年：2010
• 卷：132
• 期：26
• 页码：8915-8917
• 全文大小：211K
• 年卷期：v.132,no.26(July 7, 2010)
• ISSN：1520-5126

文摘

A broad range of highly enantioenriched 2-acylimidazoles are synthesized by palladium-catalyzed decarboxylative asymmetric allylic alkylation (DAAA) of 2-imidazolo-substituted enol carbonates. The enantioenriched 2-acylimidazole products can easily be converted to the corresponding carboxylic acid, ester, amide, and ketone derivatives with complete retention of the enantiopurity. The synthetic utility of this new method is demonstrated in the short, efficient synthesis of cetiedil.