Regiochemistry in 1,3-Dipolar Cycloadditions of the Azomethine Ylide Formed from Diethyl Aminomalonate and Paraformaldehyde

Charles M. Blazey and Clayton H. Heathcock*
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720 chh@steroid.cchem.berkeley.edu
J. Org. Chem., 2002, 67 (1), pp 298–300
DOI: 10.1021/jo010645x
Publication Date (Web): December 14, 2001
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.

Abstract

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The azomethine ylide derived from the condensation of diethyl aminomalonate with paraformaldehyde undergoes 1,3-dipolar cycloadditions with acrylate and propiolate derivatives. Contrary to a previous report, these reactions yield mixtures of regioisomers generally favoring the 2,2,3-trisubstituted product. However, the relative quantity of the 2,2,4-trisubstituted product formed increases with an increase in the size of the activating group on the dipolaroplile.

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History

  • Published In Issue January 11, 2002
  • Received June 25, 2001

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