An exceptionally simple and catalytic method for regeneration of carbonyl functionality from the corresponding 1,3-oxathiolanes

Abstract

A wide variety of 1,3-oxathiolanes 1 can be chemoselectively deprotected to the corresponding carbonyl compounds 2 in good yields by employing V₂O₅–H₂O₂ catalyzed oxidation of ammonium bromide in a CH₂Cl₂–H₂O mixture at 0–5 °C. Some of the major advantages of this procedure are its mild conditions, and that it is highly selective and efficient, high yielding, and cost-effective. Furthermore, no brominations occur at the double bond or allylic position or α to the keto position or aromatic ring.