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A Trifunctional Catalyst for a Rapid Aza-Morita-Baylis-Hillman Reaction
J.-M. Garnier, C. Anstiss, F. Liu*
mACQUARIE UNiversity, SYDNEY, australia
23 March 2009 (online)
Liu and co-workers report the design of a trifunctional catalyst 1 and its application to the enantioselective aza-Morita-Baylis-Hillman reaction. This Brønsted acid activated catalyst combines the standard nucleophilic phosphine Lewis base with two Brønsted acidic sites within the same chiral platform. Reactions of N-tosyl imines with but-3-en-2-one in the presence of protonated 1 gave the desired products after an exceptionally short time (usually three hours) and with good enantioselectivity. Careful control studies convincingly demonstrated the importance of each of the designed catalytic sites.