The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β-Unsaturated Aldehydes

Nick A. Paras and David W. C. MacMillan*
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125
J. Am. Chem. Soc., 2002, 124 (27), pp 7894–7895
DOI: 10.1021/ja025981p
Publication Date (Web): June 12, 2002
Copyright © 2002 American Chemical Society
*

 Corresponding author. E-mail:  dmacmill@caltech.edu.

Abstract

Abstract Image

The first enantioselective organocatalytic alkylation of electron-rich benzene rings with α,β-unsaturated aldehydes has been accomplished. The use of iminium catalysis has provided a new strategy for the enantioselective construction of benzylic stereogenicity, an important chiral synthon for natural product and medicinal agent synthesis. The (2S,5S)-5-benzyl-2-tert-butylimidazolidinone amine catalyst has been found to mediate the conjugate addition of a wide variety of substituted and unsubstituted anilines to unsaturated aldehydes. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 10 mol % were generally employed in this study, successful alkylations conducted with catalyst loadings as low as 1 mol % are described.

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History

  • Published In Issue July 10, 2002
  • Received February 20, 2002

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