Ag-Catalyzed Selective C–C Bond Activation of Cyclopropenones to Access α-Alkylidene Lactones

Abstract

A novel Ag-catalyzed ring opening of unsymmetric cyclopropenones for the stereoselective synthesis of a diverse range of α-alkylidene lactones has been developed. In this protocol, two different C−C(O) bonds were distinguished, demonstrating selective C−C bond activation. This reaction features a wide substrate scope, good functional group compatibility, and high atom economy, providing a versatile and general approach to the construction of α-alkylidene lactones.S tructurally diverse α-alkylidene lactones represent important units in a variety of natural compounds and biologically active molecules, such as nocardiolactone, 1a vibralactone R, 1b floribundane B, 1c and gomerolactone 1d (Figure 1). Additionally, the α-alkylidene lactone motif can ■ ASSOCIATED CONTENT Data Availability StatementThe data underlying this study are available in the published article and its Supporting Information * sı Supporting InformationThe Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.4c01853.Experimental procedures, mechanistic studies, characterization, and NMR spectra for all products (PDF)