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  • Title: Efficient asymmetric synthesis of chiral hydroxy-gamma-butyrolactones.
    Author: Davies IR, Cheeseman M, Green R, Mahon MF, Merritt A, Bull SD.
    Journal: Org Lett; 2009 Jul 02; 11(13):2896-9. PubMed ID: 19514744.
    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.
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