Fluoride-assisted regioselective conversion of functionalized furans to alpha-substituted gamma-hydroxybutenolides using singlet oxygen.
A facile synthesis of alpha-substituted gamma-hydroxybutenolides from 3-furfural was achieved using a Baylis-Hillman reaction followed by singlet oxygen oxidation. The regioselectivity of this conversion was controlled by using TBAF.
Patil
Santoshkumar N
SN
Department of Chemistry and Biomolecular Sciences, Macquarie University, Sydney, New South Wales 2109, Australia.
Liu
Fei
F
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D005459:Fluorides / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D008956:Models, Chemical; D010100:Oxygen / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D026082:Singlet Oxygen / Q000737:chemistry; D013237:Stereoisomerism
D005663:Furans; D000644:Quaternary Ammonium Compounds; D026082:Singlet Oxygen; C004511:butenolide; D015107:4-Butyrolactone; D005459:Fluorides; D010100:Oxygen