Diastereoselective 1,3-Dioxolane Formation by Photocatalytic Ring Opening of α-Epoxyketones

Abstract

Photocatalytic ring opening of alpha-epoxyketones by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in acetone resulted in the diastereoselective formation of 1,3-dioxolanes through C-alpha-O bond cleavage. The facility of the ring opening is influenced by the nature and the location of the additional substituent on the alpha-epoxyketones.