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Communication

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

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Katsuya Matsui, Shinobu Takizawa, and Hiroaki Sasai*

The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan

J. Am. Chem. Soc., 2005, 127 (11), pp 3680–3681

DOI: 10.1021/ja0500254

Publication Date (Web): March 1, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sasai@sanken.osaka-u.ac.jp

Abstract

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.

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Published In Issue March 23, 2005
Received January 4, 2005

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Communication

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

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Asymmetric Morita−Baylis−Hillman Reactions Catalyzed by Chiral Brønsted Acids

Chiral Phosphine Lewis Bases Catalyzed Asymmetric aza-Baylis−Hillman Reaction of N-Sulfonated Imines with Activated Olefins

Bifunctional Activation and Racemization in the Catalytic Asymmetric Aza-Baylis−Hillman Reaction

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