Different Reaction Patterns in the Baylis-Hillman Reaction of Aryl Aldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate and Phenyl Thioacrylate
In the Baylis-Hillman reaction of aryl aldehydes with phenyl vinyl ketone we have observed exclusive formation of diadducts 4, and that the yields of diadduct can reach 80% with increasing amounts of phenyl vinyl ketone. On the other hand, for phenyl acrylate and phenyl thioacrylate, only the normal Baylis-Hillman adduct was obtained. The effects of substituents were also examined and a plausible reaction mechanism is proposed for the formation of compounds 4.
A unique cascade reaction between 3-arylprop-2-inylcarboxylates and benzaldehydes leading to the formation of Morita-Baylis-Hillman adducts.
During an alkyne-carbonyl metathesis reaction between electron-rich 3-arylprop-2-inylcarboxylates and electron-poor benzaldehydes, a smooth migration of carboxylate groups takes place. This unique cascade reaction allows the formation of Morita-Baylis-Hillman (MBH) adducts unavailable via a traditional MBH reaction.
Catalytic enantioselective Baylis-Hillman reactions. Correlation between pressure and enantiomeric excess
Several chiral amino-alcohols induce asymmetry in the Baylis-Hillman condensation of aldehydes with methyl vinyl ketone. Pressure plays an interesting role in this reaction. A model accounting for the pressure effect and rationalising the observed absolute stereochemistry is discussed. Copyright (C) 1996 Elsevier Science Ltd