title: Efficient asymmetric synthesis of chiral hydroxy-gamma-butyrolactones.
abstract: Treatment of beta-vinyl-beta-hydroxy-N-acyloxazolidin-2-ones with VO(acac)(2) and tert-butyl hydroperoxide results in formation of unstable epoxides that are ring-opened by intramolecular nucleophilic attack of their exocyclic carbonyl fragments to afford highly functionalized trisubstituted hydroxy-gamma-butyrolactones in >95% de, with a polymer-supported oxazolidin-2-one having been used to transfer this methodology to the solid phase.
authors.affiliation: Department of Chemistry, University of Bath, BA2 7AY, UK.
authors.forename: Iwan R
authors.initials: IR
authors.lastname: Davies
authors.forename: Matt
authors.initials: M
authors.lastname: Cheeseman
authors.forename: Rachel
authors.initials: R
authors.lastname: Green
authors.forename: Mary F
authors.initials: MF
authors.lastname: Mahon
authors.forename: Andrew
authors.initials: A
authors.lastname: Merritt
authors.forename: Steven D
authors.initials: SD
authors.lastname: Bull
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D023303:Oxazolidinones; D015107:4-Butyrolactone