American Chemical Society
ol303312p_si_003.cif (18.98 kB)

Asymmetric Vinylogous Aldol Reaction via H‑Bond-Directing Dienamine Catalysis

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posted on 2013-01-04, 00:00 authored by David Bastida, Yankai Liu, Xu Tian, Eduardo Escudero-Adán, Paolo Melchiorre
The enantioselective direct vinylogous aldol reaction of 3-methyl 2-cyclohexen-1-one with α-keto esters has been developed. The key to success was the design of a bifunctional primary amine-thiourea catalyst that can combine H-bond-directing activation and dienamine catalysis. The simultaneous dual activation of the two reacting partners results in high reactivity while securing high levels of stereocontrol.