A direct, catalytic method for the synthesis of γ-butyrolactones from simple alkene and unsaturated acids is reported. The catalytic system consists of the Fukuzumi acridinium photooxidant and substoichiometric quantities of phenyl disulfide as a redox-active cocatalyst. Oxidizable alkenes such as styrenes and tri-substituted alkenes are cyclized with a variety of unsaturated acids via polar radical crossover cycloaddition (PRCC) reactions. Unsaturated acids such as mono-ester maleic acids and cinnamic acids are well tolerated. Additionaly, a variety of α-alkylidine γ-butyrolactones can be produced by using alkynyl unsaturated acids. The method is applied to the diastereoselective synthesis of the α-methylene Paraconic acids methylenolactocin and protolichesterinic acid.

Butyrolactone synthesis via polar radical crossover cycloaddition reactions: Diastereoselective synthesis of methylenolactocin and protolichesterinic acid

249th National Meeting (2015)

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