Transition-Metal-Free Hydrogen Autotransfer: Diastereoselective N-Alkylation of Amines with Racemic Alcohols.

A practical method for the synthesis of alpha-chiral amines that is based on the alkylation of amines with alcohols and does not require any transition-metal catalysts is described by M. Lei, J. L. Xiao, C. Wang, and co-workers in their Research Article (DOI: 10.1002/anie.201905870). With a ketone and NaOH as co-catalysts, racemic alcohols react with Ellman's chiral sulfinamide, affording chiral amines with high diastereoselectivities. This method also provides access to chiral deuterium-labeled amines and drug molecules.