The Au(I)-catalyzed asymmetric cascade cyclization of yne-enones/addition represents a powerful strategy for constructing furan skeletons; however, the use of enol-type carbon nucleophiles in this transformation remains a considerable challenge. In this study, we report the development of a novel bio-inspired chiral multifunctional phosphine ligand and its application in Au(I)-catalyzed highly diastereo- and enantioselective cyclization of yne-enones/enol-addition. The catalytic system tolerated a broad range of substrates, for the first time, providing access to furan products bearing consecutive stereocenters via this reaction type. Control experiments and DFT calculations underscore the validity of our cooperative multifunctional design, wherein modular multiple chiral centers and tailored noncovalent interactions collectively account for the excellent stereocontrol and high chemoselectivity observed.
Li et al. (Mon,) studied this question.