Copper-catalyzed, stereoconvergent, cis-diastereoselective borylative cyclization of ω-mesylate-α,ß-unsaturated esters and ketones.

ABSTRACT

The Cu(i)-catalyzed stereoconvergent borylative cyclization of ω-mesylate-α,ß-unsaturated compounds is facilitated by a simple Cu-bisphosphine catalyst. This reaction provides a novel route to cis-ß-boron-substituted five- and six-membered carbocycle and heterocycle esters. Mechanistic studies indicate that stereoconvergence and cis-substitution likely stem from the rapid enolation of the borylcopper adduct with the substrate double bond and the formation of a five-membered intermediate, respectively.