Effect of branching in alkylgroups of tertiary amines on their performance as catalysts in the high pressure promoted Bylis-Hillman reaction

Article abstract of DOI:10.1016/0040-4020(96)00384-5

Receptors 1 were tested as catalysts for the high pressure promoted Baylis-Hillman reaction. Surprisingly most of the compounds were found to be catalytically inactive. With model compounds (simple acyclic tertiary amines) it could be shown that tertiary amines with branches at their α-carbon atoms show a remarkable decreased activity. It is proposed that the branches prevent attack of the lone pair of the amine on the double bond of the alkene. This explains why only receptors without this feature are catalytically active.