Synthesis by chiral diamine-mediated asymmetric alkylation

A method for making a chiral alkylated derivative of a nitrogen-containing heterocycle, comprising:

• incorporating into a medium with an α-substitutable-N-heterocycle at least an organometallic compound, a chiral diamine, a strained cyclic ether, and a Lewis acid, wherein:
• the α-substitutable-N-heterocycle is selected from the group consisting of aziridine, azetidine, azepane, pyrrolidine, piperidine, hexahydroazepine, azocane, imidazolidine, pyrazolidine, hexahydropyridazine, hexahydropyrimidine, piperazine, and mixtures thereof, and forms of such heterocycles that have at least one protected amino group;
• the organometallic compound is an organolithium;
• and
• the chiral diamine is (+)-sparteine, (−)-sparteine, (+)-sparteine surrogate, or a salt or stereoisomer thereof.