A One-Pot C鈥揌 Insertion/Olefination Sequence for the Formation of 伪-Alkylidene-纬-butyrolactones

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• 作者：Matthew G. Lloyd ; Richard J. K. Taylor ; William P. Unsworth
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：May 16, 2014
• 年：2014
• 卷：16
• 期：10
• 页码：2772-2775
• 全文大小：335K
• 年卷期：v.16,no.10(May 16, 2014)
• ISSN：1523-7052

文摘

A one-pot C鈥揌 insertion/olefination sequence for the conversion of 伪-diazo-伪-(dialkoxyphosphoryl)acetates into 伪-alkylidene-纬-butyrolactones is reported. The key C鈥揌 insertion process is achieved using a catalytic amount of a dirhodium carboxylate catalyst, using operationally simple conditions. The size and electronic properties of the attached substituents were found to influence the regio- and diastereoselectivity of the process. The utility of the process is demonstrated by the synthesis of a known Staphylococcus aureus (MRSA) virulence inhibitor.