Catalytic asymmetric C-N bond formation: phosphine-catalyzed intra- and intermolecular γ-addition of nitrogen nucleophiles to allenoates and alkynoates.

Abstract

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,β-unsaturated carbonyl compounds.