Synthesis of Enantioenriched α,α-Disubstituted Cyclopentenes Catalyzed by N-Heterocyclic Carbenes

Abstract

The desymmetrization of 1,3-diketones using N-heterocyclic carbenes results in the formation of highly enantioenriched cyclopentenes in good yield. The reaction proceeds through a catalytic intramolecular aldol reaction and subsequent β-lactone formation. The expulsion of carbon dioxide at mild reaction temperatures affords the cyclopentene products.