Dramatic Rate Acceleration of the Baylis−Hillman Reaction in Homogeneous Medium in the Presence of Water

Juexiao Cai, Zhenghong Zhou, Guofeng Zhao, and Chuchi Tang*
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
Org. Lett., 2002, 4 (26), pp 4723–4725
DOI: 10.1021/ol027197f
Publication Date (Web): December 6, 2002
Copyright © 2002 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.

, c.c.tang@eyou.com

Abstract

Abstract Image

In homogeneous H2O/solvent medium, the reaction rate of aromatic aldehydes and acrylonitrile or acrylate was greatly accelerated, which led to shorter reaction time, lower reaction temperature, and higher yield. In this reaction, Me3N, DMAP, DABCO, and urotropine were good catalysts. Except for low-carbon alcohols, tetrahydrofuran, 1,4-dioxane, and acetonitrile could be chosen as the solvent. Under this condition, the diastereoselective reaction of nitrobenzaldehyde and l-menthyl acrylate was realized with 88−99% de.

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  • Published In Issue December 26, 2002
  • Received October 29, 2002

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