Asymmetric Amination of Primary Alcohols via Dynamic Kinetic Resolution: Enantioconvergent Access to Chiral Benzomorpholines

Abstract

We present here a catalytic enantioconvergent amination of alcohols for efficient access to chiral C2- and C3-substituted benzomorpholines. The racemic amino alcohol substrates of different substitution patterns, which are readily available from a common precursor, can be converted to the enantioenriched heterocycles in a highly atom- and step-economical fashion. In particular, an unprecedented asymmetric amination of racemic primary alcohols via dynamic kinetic resolution is achieved under cooperative iridium/iron catalysis, resulting in highly enantioenriched C2-substituted benzomorpholines that are difficult to access otherwise.