A one-pot, base-free annelation approach to alpha-alkylidene-gamma-butyrolactones.
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.
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
Russell R A
RR
Kitson
Richard J K
RJ
Taylor
John L
JL
Wood
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D015107:4-Butyrolactone