Asymmetric three-component propargyloxylation for direct assembly of polyfunctionalized chiral succinate derivatives

An enantioselective three-component propargyloxylation reaction of propargyl alcohols, pyridotriazoles, and imines has been realized by cooperative catalysis with dirhodium complex and chiral phosphoric acid under mild conditions. This is the first example of a catalytic asymmetric three-component propargyloxylation reaction, which provides practical access to chiral polyfunctionalized succinate derivatives with adjacent quaternary and tertiary stereocenters in good to high yields with excellent enantioselectivity. In addition to the alkyne motif, pyridyl, alkoxy, amino, and alkenyl species are all tolerated under the reaction conditions. Notably, the utility of the current method is demonstrated by catalytic cyclization of the product alkyne into a variety of heterocyclic structures without loss of enantiomeric purity.