Regioselective synthesis and structural studies of substituted γ-hydroxybutenolides with use of a tandem baylis-hillman/singlet oxygenation reaction

Santoshkumar N. Patil; Fei Liu

doi:10.1021/jo702762u

Regioselective synthesis and structural studies of substituted γ-hydroxybutenolides with use of a tandem baylis-hillman/singlet oxygenation reaction

Santoshkumar N. Patil, Fei Liu^*

^*Corresponding author for this work

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

16 Citations (Scopus)

Abstract

(Chemical Equation Presented) The scope and limitations of a regioselective synthesis of either α- or β-substituted γ-hydroxybutenolides from 3-furfural and enones are described. The sequence features a Baylis-Hillman reaction followed by singlet oxygen oxidation with use of either an amine base or TBAF as the regioselectivity switches. Structural studies in solution on some of the resulting γ-hydroxybutenolides are also reported.

Original language	English
Pages (from-to)	4476-4483
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	73
Issue number	12
DOIs	https://doi.org/10.1021/jo702762u
Publication status	Published - 20 Jun 2008

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abstract = "(Chemical Equation Presented) The scope and limitations of a regioselective synthesis of either α- or β-substituted γ-hydroxybutenolides from 3-furfural and enones are described. The sequence features a Baylis-Hillman reaction followed by singlet oxygen oxidation with use of either an amine base or TBAF as the regioselectivity switches. Structural studies in solution on some of the resulting γ-hydroxybutenolides are also reported.",

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N2 - (Chemical Equation Presented) The scope and limitations of a regioselective synthesis of either α- or β-substituted γ-hydroxybutenolides from 3-furfural and enones are described. The sequence features a Baylis-Hillman reaction followed by singlet oxygen oxidation with use of either an amine base or TBAF as the regioselectivity switches. Structural studies in solution on some of the resulting γ-hydroxybutenolides are also reported.

AB - (Chemical Equation Presented) The scope and limitations of a regioselective synthesis of either α- or β-substituted γ-hydroxybutenolides from 3-furfural and enones are described. The sequence features a Baylis-Hillman reaction followed by singlet oxygen oxidation with use of either an amine base or TBAF as the regioselectivity switches. Structural studies in solution on some of the resulting γ-hydroxybutenolides are also reported.

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Regioselective synthesis and structural studies of substituted γ-hydroxybutenolides with use of a tandem baylis-hillman/singlet oxygenation reaction

Abstract

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