CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines

This
report details a general and enantioselective means for the
synthesis of alkyl-substituted aziridines. This protocol offers a
direct route for the synthesis of alkyl-substituted chiral aziridines
from achiral starting materials. Readily accessed allylic hydroxylamine
esters undergo copper hydride-catalyzed intramolecular hydroamination
with a high degree of regio- and enantiocontrol to afford the aziridine
products in good to excellent yields in highly enantioenriched form.
The utility of the products derived from this method is further demonstrated
through derivatization of the chiral aziridine products to obtain
a diverse array of functionalized enantioenriched amines.