Radical decarboxylative alkylation of tartaric acid

Article abstract of DOI:10.1016/S0040-4020(01)81288-6

New derivatives of L-(+)-tartaric acid have been synthesized from the monomethyl-2,3-O-isopropylidene (R,R)-(+)-tartrate by visible light photolysis of its N-hydroxy-2-thiopyridone ester derivative in presence of activate alkenes. The carbon radical generated at the dioxolane ring adds stereoselectively to olefins to give the addition products with retention of configuration.