N-Spiro Chiral Quaternary Ammonium Bromide Catalyzed Diastereo- and Enantioselective Conjugate Addition of Nitroalkanes to Cyclic α,β-Unsaturated Ketones under Phase-Transfer Conditions

Takashi Ooi, Saki Takada, Shingo Fujioka, and Keiji Maruoka*
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
Org. Lett., 2005, 7 (23), pp 5143–5146
DOI: 10.1021/ol0517170
Publication Date (Web): October 14, 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

Abstract Image

Conjugate addition of various prochiral nitroalkanes to cyclic α,β-unsaturated ketones was found to be efficiently catalyzed by N-spiro C2-symmetric chiral quaternary ammonium bromide 1b possessing a 3,5-bis(3,4,5-trifluorophenyl)phenyl substituent under solid−liquid phase-transfer conditions to afford the corresponding γ-nitro ketones in excellent chemical yields with unprecedented levels of diastereo- and enantiocontrol.

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History

  • Published In Issue November 10, 2005
  • Received July 20, 2005

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