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

Katsuya Matsui, Shinobu Takizawa, and Hiroaki Sasai*

*The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan, Email: sasaisanken.osaka-u.ac.jp

K. Matsui, S. Takizawa, H. Sasai, J. Am. Chem. Soc., 2005, 127, 3680-3681.

DOI: 10.1021/ja0500254 (free Supporting Information)


Abstract

(S)-3-(N-Isopropyl-N-3-pyridinylaminomethyl)BINOL is an efficient, bifunctional organocatalyst for the enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reaction. 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.

see article for more examples and reactions



A Brønsted Acid and Lewis Base Organocatalyst for the Aza-Morita-Baylis-Hillman Reaction

K. Matsui, S. Takizawa, H. Sasai, Synlett, 2006, 761-765.


Key Words

Organocatalysis, Baylis-Hillman Reaction, Allylamines


ID: J48-Y2005-2290