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Bifunctional Organocatalysts for Enantioselective aza-Morita−Baylis−Hillman Reaction

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journal contribution
posted on 23.03.2005, 00:00 authored by Katsuya Matsui, Shinobu Takizawa, Hiroaki Sasai
The efficient and novel bifunctional organocatalyst for the enantioselective aza-Morita−Baylis−Hillman (aza-MBH) reaction has been established with (S)-3-(N-isopropyl-N-3-pyridinylaminomethyl)BINOL for the first time. The reaction proved to be deeply influenced by the position of the Lewis base attached to BINOL. The acid−base-mediated functionalities for the activation of the substrate and the fixing of conformation of the organocatalyst are harmoniously performed to promote the reaction with high enantiocontrol.