Communication

Enantioselective Michael Addition of Dicyanoolefins to α,β-Unsaturated Aldehydes in Aqueous Medium

  1. Jun Lu,
  2. Feng Liu,
  3. Teck-Peng Loh

Article first published online: 24 JUL 2008

DOI: 10.1002/adsc.200800145

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 350, Issue 11-12, pages 1781–1784, August 4, 2008

Additional Information

How to Cite

Lu, J., Liu, F. and Loh, T.-P. (2008), Enantioselective Michael Addition of Dicyanoolefins to α,β-Unsaturated Aldehydes in Aqueous Medium. Adv. Synth. Catal., 350: 1781–1784. doi: 10.1002/adsc.200800145

Author Information

  1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 1 Nanyang Link, Singapore 637371, Fax: (+65)-6791-1961; phone: (+65)-6316-8899

Publication History

  1. Issue published online: 31 JUL 2008
  2. Article first published online: 24 JUL 2008
  3. Manuscript Received: 11 MAR 2008

Funded by

  • Biomedical Research Council. Grant Number: M47110003

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Keywords:

  • dicyanoolefins;
  • enantioselective Michael addition;
  • organocatalysts;
  • unsaturated aldehydes;
  • water

Abstract

A pool of water-compatible catalysts, namely dialkyl-(S)-prolinols, has been developed for the enantioselective direct vinylogous Michael addition reaction of vinylmalononitriles to α,β-unsaturated aldehydes in aqueous medium. In many cases, the products can be obtained in almost optically pure form (>96% ee) after a single recrystallization.

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