Regioselective synthesis and structural studies of substituted gamma-hydroxybutenolides with use of a tandem Baylis-Hillman/singlet oxygenation reaction.
The scope and limitations of a regioselective synthesis of either alpha- or beta-substituted gamma-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 gamma-hydroxybutenolides are also reported.
Patil
Santoshkumar N
SN
Department of Chemistry & Biomolecular Sciences, Macquarie University, Sydney, NSW, Australia.
Liu
Fei
F
D000440:Butanols / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D013237:Stereoisomerism
D000440:Butanols; D010100:Oxygen