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revised on 17.09.2018 and posted on 17.09.2018by Dhananjayan Vasu, Ángel L. Fuentes de Arriba, Jamie Leitch, Antoine de Gombert, Darren J. Dixon
A quinone-mediated general platform for the
construction of primary α-tertiary amines from abundant primary α-branched amine
starting materials is described. This procedure pivots on the efficient in situ
generation of reactive ketimine intermediates and subsequent reaction with
carbon-centered nucleophiles such as organomagnesium and organolithium
reagents, and TMSCN, creating quaternary centers. Furthermore, extension to
reverse polarity photoredox catalysis enables reactivity with electrophiles.
This efficient, broadly applicable and scalable amine-to-amine synthetic
platform was successfully applied to library and API synthesis and in the late
stage functionalization of drug molecules.