Photoredox-catalyzed hydroxymethylation of β-ketoesters: application to the synthesis of [3.3.3] propellane lactones

Abstract

Photoredox-catalysed hydroxymethylation of β-ketoesters substituted by an allyl subunit on the α-position afforded directly the corresponding bicyclic lactones possessing both a hydroxy group and an unsaturation. A subsequent regioselective iodoetherification led to the formation of original [3.3.3] propellane structures. Substitution of the iodine atom by various nucleophiles afforded highly functionnalized structures including triazolomethyl derivatives.