A one-pot, base-free annelation approach to alpha-alkylidene-gamma-butyrolactones

Russell R A Kitson; Richard J K Taylor; John L Wood

doi:10.1021/ol902191d

A one-pot, base-free annelation approach to alpha-alkylidene-gamma-butyrolactones

Org Lett. 2009 Nov 19;11(22):5338-41. doi: 10.1021/ol902191d.

Authors

Russell R A Kitson¹, Richard J K Taylor, John L Wood

Affiliation

¹ Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.

PMID: 19860387
DOI: 10.1021/ol902191d

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemical synthesis*
4-Butyrolactone / chemistry
Molecular Structure
Stereoisomerism

Substances

4-Butyrolactone