Enantioselective Transformations from Nitriles to NH2-α-Tertiary Amines

Organic molecules, containing one or more amine chiral centers, are very common to see in natural products and medicines. Although a large number of methods have been developed to afford enantiopure amines, most of the known approaches are limited with various reasons. For example, many methodologies start from nitrogen protected and activated substrates, which usually need multistep operations and seriously decrease the atom economy. Here we disclose a new catalytic strategy from commercial nitriles to high enantioselective alpha-tertiary primary amines in up to 90 % yield and 95 % enantiomeric excess. This transformation firstly undergoes an addition process of organolithium reagents to nitriles to generate the imine intermediates in situ. Subsequently, the most challenging step is by employing copper catalytic enantioselective addition of AllylBpin to the imine intermediates to form the final amines in one pot.

Automated summary

In this study, a new catalytic strategy for the synthesis of α-tertiary primary amines from commercial nitriles is reported. The method involves the addition of organolithium reagents to nitriles to generate imine intermediates, followed by copper catalyzed enantioselective addition of AllylBpin to form the final amines. This strategy offers high yields (up to 90%) and excellent enantiomeric excess (95%).