Asymmetric 1,3-Dipolar Cycloaddition Reaction of Nitrones and Acrolein with a Bis-Titanium Catalyst as Chiral Lewis Acid

Taichi Kano, Takuya Hashimoto, and Keiji Maruoka*
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
J. Am. Chem. Soc., 2005, 127 (34), pp 11926–11927
DOI: 10.1021/ja0523284
Publication Date (Web): August 4, 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

A μ-oxo-type chiral bis-Ti(IV) oxide (S,S)-1 can be successfully utilized in the asymmetric 1,3-dipolar cycloaddition reactions between various nitrones 2 and acrolein to give the corresponding isoxazolidines with high to excellent enantioselectivities. For instance, the reaction between nitrone 2 (R = t-Bu) and acrolein in the presence of 10 mol % of bis-Ti(IV) catalyst (S,S)-1 in dichloromethane at −40 °C gave the corresponding endo cycloadduct with 97% ee.

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History

  • Published In Issue August 31, 2005
  • Received April 11, 2005

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