Importance of Chiral Phase-Transfer Catalysts with Dual Functions in Obtaining High Enantioselectivity in the Michael Reaction of Malonates and Chalcone Derivatives

Takashi Ooi, Daisuke Ohara, Kazuhiro Fukumoto, and Keiji Maruoka*
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
Org. Lett., 2005, 7 (15), pp 3195–3197
DOI: 10.1021/ol050902a
Publication Date (Web): June 28, 2005
Copyright © 2005 American Chemical Society
*

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

, maruoka@kuchem.kyoto-u.ac.jp

Abstract

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Highly enantioselective Michael addition of diethyl malonate to chalcone derivatives has been achieved under mild phase-transfer conditions by the successful utilization of N-spiro C2-symmetric chiral quaternary ammonium bromide 1 as a catalyst, which possesses diarylhydroxymethyl functionalities as a recognition site for the prochiral electrophile. This simple asymmetric Michael addition process was found to be quite effective for various chalcone derivatives, including those with heteroaromatic substituents.

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History

  • Published In Issue July 21, 2005
  • Received April 22, 2005

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