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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.

Details

Item Type Articles
CreatorsDavies, I. R., Cheeseman, M., Green, R., Mahon, M. F., Merritt, A. and Bull, S. D.
DOI10.1021/ol9008365
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code15298

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