Regioselective ring opening and isomerization reactions of 3,4-epoxyesters catalyzed by boron trifluoride

Org Lett. 2011 Aug 5;13(15):3856-9. doi: 10.1021/ol201378w. Epub 2011 Jul 6.

Abstract

Efficient ring opening of 3,4-epoxyesters with alcohols to produce 4-alkoxy-3-hydroxyesters and their isomerization into 4-ketoesters using boron trifluoride as the catalyst are presented. Both transformations are simple and efficient methods for the synthesis of the above named synthetically useful compounds.