Catalytic Asymmetric CN Bond Formation: Phosphine-Catalyzed Intra- and Intermolecular [gamma]-Addition of Nitrogen Nucleophiles to Allenoates and Alkynoates

Pin the amine on the gamma: A new method has been developed for the γ-addition of nitrogen nucleophiles to γ-substituted alkynoates or allenoates through intra- and intermolecular processes that are catalyzed by spirophosphine 1. An asymmetric version of this reaction affords enantioenriched pyrrolidines, indolines, and γ-amino-α,[beta]-unsaturated carbonyl compounds.