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A One-Pot, Base-Free Annelation Approach to alpha-Alkylidene-gamma-butyrolactones

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JournalOrganic Letters
DatePublished - 19 Nov 2009
Issue number22
Volume11
Number of pages4
Pages (from-to)5338-5341
Original languageEnglish

Abstract

A novel annelation procedure has been developed for the conversion of gamma-hydoxy enones into alpha-alkylidene-gamma-butyrolactones. This one-pot method utilizes the Bestmann ylide (triphenylphosphoranylideneketene) and proceeds by way of acylation followed by an intramolecular conjugate addition/proton transfer/Wittig olefination sequence. The procedure is "base-free" and is useful for the preparation of a range of alpha-alkylidene-gamma-butyrolactones including alpha-methylene-gamma-butyrolactone examples, which can be particularly base-sensitive.

    Research areas

  • (+)-PAEONILACTONE-B, OLEFINATION, YLIDES

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