Chiral Diols:  A New Class of Additives for Direct Aldol Reaction Catalyzed by l-Proline

Yan Zhou and Zixing Shan*
Department of Chemistry, Wuhan University, Wuhan 430072, China zxshan@whu.edu.cn
J. Org. Chem., 2006, 71 (25), pp 9510–9512
DOI: 10.1021/jo060802y
Publication Date (Web): November 15, 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.

Abstract

Abstract Image

Nine C2 symmetric diols have been examined as additives in the l-proline-catalyzed direct aldol reaction with significant improvement in enantioselectivity, conversion efficiency, and yield. Loading of 1 mol % of (S)-BINOL leads to the desired products in up to 98% ee and 90% yield. A transition state is proposed.

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History

  • Published In Issue December 08, 2006
  • Received April 16, 2006

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