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A One-Pot C-H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones

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JournalOrganic Letters
DateE-pub ahead of print - 2 May 2014
DatePublished (current) - 2014
Issue number10
Volume16
Number of pages4
Pages (from-to)2772-2775
Early online date2/05/14
Original languageEnglish

Abstract

A one-pot C-H insertion/olefination sequence for the conversion of α-diazo-α-(dialkoxyphosphoryl)acetates into α-alkylidene-γ-butyrolactones is reported. The key C-H 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.

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