Regio- and stereoselective acylation of saturated carbocycles via Norrish–Yang photocyclization

Abstract

A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish–Yang photocyclization of 1,2-diketones and subsequent ring opening of the α-hydroxy-cyclobutanones. The C–H activation of the carbocycle proceeds regioselectively at vicinal to the diketone moiety resulting in stereoselective formation of cis-fused bicycles. The following C–C cleavage affords vicinally cis-acylated carbocycles. Predictability, generality, and practicality of the present strategy have been demonstrated using variously modified saturated carbocycles.