Synfacts 2009(4): 0447-0447  
DOI: 10.1055/s-0028-1088104
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

A Trifunctional Catalyst for a Rapid Aza-Morita-Baylis-Hillman Reaction

Contributor(s): Benjamin List, Olga Lifchits
J.-M. Garnier, C. Anstiss, F. Liu*
mACQUARIE UNiversity, SYDNEY, australia
Further Information

Publication History

Publication Date:
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.