Efficient Asymmetric Synthesis of Chiral Hydroxy-γ-butyrolactones

Iwan R Davies; M Cheeseman; R Green; Mary F Mahon; A Merritt; Steven D Bull

doi:10.1021/ol9008365

Efficient Asymmetric Synthesis of Chiral Hydroxy-γ-butyrolactones

Iwan R Davies, M Cheeseman, R Green, Mary F Mahon, A Merritt, Steven D Bull

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

16 Citations (SciVal)

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.

Original language	English
Pages (from-to)	2896-2899
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	13
DOIs	https://doi.org/10.1021/ol9008365
Publication status	Published - 2009

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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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journal = "Organic Letters",

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T1 - Efficient Asymmetric Synthesis of Chiral Hydroxy-γ-butyrolactones

AU - Davies, Iwan R

AU - Cheeseman, M

AU - Green, R

AU - Mahon, Mary F

AU - Merritt, A

AU - Bull, Steven D

PY - 2009

Y1 - 2009

N2 - 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.

AB - 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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UR - http://dx.doi.org/10.1021/ol9008365

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VL - 11

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JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Efficient Asymmetric Synthesis of Chiral Hydroxy-γ-butyrolactones

Abstract

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