Regiochemistry in 1,3-dipolar cycloadditions of the azomethine ylide formed from diethyl aminomalonate and paraformaldehyde.

Charles M Blazey, Clayton H Heathcock

Index: J. Org. Chem. 67(1) , 298-300, (2002)

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Abstract

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.