Axially Chiral Guanidine as Enantioselective Base Catalyst for 1,4-Addition Reaction of 1,3-Dicarbonyl Compounds with Conjugated Nitroalkenes

Masahiro Terada,* Hitoshi Ube, and Yusuke Yaguchi
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
J. Am. Chem. Soc., 2006, 128 (5), pp 1454–1455
DOI: 10.1021/ja057848d
Publication Date (Web): January 11, 2006
Copyright © 2006 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.

, mterada@mail.tains.tohoku.ac.jp

Abstract

Abstract Image

A new strategy for designing chiral guanidine molecules is presented, which features the introduction of an axially chiral binaphthyl backbone. The axially chiral guanidine catalysts thus developed facilitated the highly enantioselective 1,4-addition reaction of 1,3-dicarbonyl compounds with a broad range of conjugated nitroalkenes and showed extremely high catalytic activity.

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History

  • Published In Issue February 08, 2006
  • Received November 18, 2005

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