Propargylic Amination Enabled the Access to Enantioenriched Acyclic α-Quaternary α-Amino Ketones

Abstract

A propargylic amination approach toward chiral acyclic α-quaternary α-amino ketones is described. This Cu-catalyzed procedure could be performed open to air using commercially available amines as nucleophiles. The key to success is the use of rationally designed propargylic cyclic carbonates as substrates, which can generate a Cu-bonded enolate zwitterionic intermediate upon decarboxylation. This protocol features wide functional group tolerance and high asymmetric induction, with typical ee value higher than 93%, and thus advances a great step forward in the challenging synthesis of acyclic chiral α-quaternary α-amino ketones.