Communication

A Diarylprolinol in an Asymmetric, Catalytic, and Direct Crossed-Aldol Reaction of Acetaldehyde†

  1. Yujiro Hayashi Prof. Dr.,
  2. Takahiko Itoh,
  3. Seiji Aratake,
  4. Hayato Ishikawa Dr.

Article first published online: 8 FEB 2008

DOI: 10.1002/anie.200704870

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 11, pages 2082–2084, February 28, 2008

Additional Information

How to Cite

Hayashi, Y., Itoh, T., Aratake, S. and Ishikawa, H. (2008), A Diarylprolinol in an Asymmetric, Catalytic, and Direct Crossed-Aldol Reaction of Acetaldehyde. Angew. Chem. Int. Ed., 47: 2082–2084. doi: 10.1002/anie.200704870

Author Information

  1. Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631 http://www.ci.kagu.tus.ac.jp/lab/org-chem1/

  1. †

    This work was partially supported by the Toray Science Foundation and by a Grant-in-Aid for Scientific Research from MEXT.

Publication History

  1. Issue published online: 22 FEB 2008
  2. Article first published online: 8 FEB 2008
  3. Manuscript Received: 20 OCT 2007

Funded by

  • Toray Science Foundation
  • MEXT

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Keywords:

  • acetaldehyde;
  • aldol reaction;
  • asymmetric catalysis;
  • organocatalysis
Thumbnail image of graphical abstract

No over-reacting: A diarylprolinol was found to be an effective organocatalyst of the direct, enantioselective aldol reaction of acetaldehyde, affording β-hydroxy α-unsubstituted aldehydes in good yield with excellent enantioselectivity (see scheme). In the proposed transition state the aldehyde reacts on the more hindered face of the intermediate enamine as a consequence of the hydrogen bond between the aldehyde and the OH group of the organocatalyst.

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