Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2‑Azaallyl Anion Benzylic Ring-Opening of Aziridines

The 1,3-diamine motif
appears in numerous complex molecules, yet
there are few methods for the stereoselective construction of this
moiety. Herein, we demonstrate a stereocontrolled synthesis of 1,3-diamines,
which bear up to three contiguous stereogenic centers, through benzylic
ring-opening of aziridines with 2-azaallyl anion nucleophiles. Reactions
proceed efficiently (yield up to 95%), diastereoselectively (dr up
to >20:1), site selectively, and enantiospecifically to deliver
products
with differentiated amino groups.