Efficient Asymmetric Synthesis of Chiral Hydroxy-γ-butyrolactones

Reference:

Davies, I. R., Cheeseman, M., Green, R., Mahon, M. F., Merritt, A. and Bull, S. D., 2009. Efficient Asymmetric Synthesis of Chiral Hydroxy-γ-butyrolactones. Organic Letters, 11 (13), pp. 2896-2899.

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Official URL:

http://dx.doi.org/10.1021/ol9008365

Abstract

Treatment of β-vinyl-β-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-γ-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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