Organocatalytic asymmetric direct vinylogous aldol reactions of γ-crotonolactone with aromatic aldehydes.
The direct aldol reaction of γ-crotonolactone and various aromatic aldehydes is catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts to provide diastereomerically and enantiomerically enriched 5-substituted 2(5H) furanones (γ-butenolides). The reaction is a simple alternative to the classical vinylogous aldol reaction of silyloxy furans.
Department of Chemistry, Memorial University, St. John's, Newfoundland, Canada A1B 3X7. spansare@mun.ca
Sunil V
SV
Pansare
Eldho K
EK
Paul
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D012663:Semicarbazides / Q000737:chemistry
D000447:Aldehydes; D005663:Furans; D012663:Semicarbazides; C005151:thiosemicarbazide; C004511:butenolide; D015107:4-Butyrolactone