title: 4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions.
abstract: Two mild and efficient strategies have been developed for the O-functionalisation of 4-hydroxy-6-alkyl-2-pyrones, by using them as nucleophilic partners in oxa-Michael additions and the Mitsunobu reaction. The reactions proceed in moderate to excellent yields on a range of substrates containing useful functionality. The reactions serve as practical and valuable synthetic methods to construct complex 2-pyronyl ethers, which are found embedded in a number of natural products.
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, U.K.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Burns
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, U.K.
authors.forename: Thomas O
authors.initials: TO
authors.lastname: Ronson
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, U.K.
authors.forename: Richard J K
authors.initials: RJ
authors.lastname: Taylor
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, U.K.
authors.forename: Ian J S
authors.initials: IJ
authors.lastname: Fairlamb
keywords: 2-pyrone; Mitsunobu reaction; heterocycles; oxa-Michael addition; vinyl ethers