The Preparation of 5-Aryl-5-methyl-4,5-dihydroisoxazoles from Dilithiated C(α),O-Oximes and Select Acetyl Ketones

Abstract

Several 5-aryl-5-methyl-4,5-dihydroisoxazoles were prepared by a three-step, one-pot process in 24–83% yield. C(α),O-oximes were dilithiated with lithium diisopropylamide and condensed with electron enriched acetophenones, such as 4′-methoxyacetophenone, followed by immediate acid cyclization.

Acknowledgments

We are appreciative of the financial support from the South Carolina Research Initiatives Grant Program, grant number ROO-T08, The Petroleum Research Fund administered by the American Chemical Society, and the National Science Foundation Research in Undergraduate Institutions, grant number CHE-0212699.