Regioselective addition reaction of organolanthanide reagents to α,β-unsaturated imines

Abstract

Organolanthanum reagents[RLaCl 2] generated in situ from LaCl 3 and alkyl lithium or allyl magnesium could undergo a highly regioselective 1,2-addition to N-alkyl α,β-unsaturated imines, which provided a new and useful approach to synthesize allyl amines with good yields and high regioselectivity. Furthermore, for N-chiral alkyl α,β-unsaturated imine, in the case of n-butyl lithium, the diastereoselectivity achieved highly 90%.