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 journalArticle

21 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 languageEnglish
Pages (from-to)4476-4483
Number of pages8
JournalJournal of Organic Chemistry
Volume73
Issue number12
DOIs
Publication statusPublished - 20 Jun 2008

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