Radicals from Epoxides. Intramolecular Addition to Aldehyde and Ketone Carbonyls

Abstract

Titanocene chloride reacts with epoxides by C−O homolysis with clean regioselectivity. The resultant radicals undergo intramolecular addition to aldehyde and ketone carbonyls to afford cycloalkanols in good yields. The behavior of epoxy alcohols with titanocene chloride to afford saturated diols and epoxy esters that give unsaturated hydroxy esters deserve special mention.