REGIOSELECTIVE ADDITION-REACTION OF ORGANOLANTHANIDE REAGENTS TO ALPHA,BETA-UNSATURATED IMINES

Organolanthanum reagents[RLaCl2] generated in situ from LaCl3 and alky l lithium or allyl magnesium could undergo a highly regioselective 1,2 -addition to N-alkyl alpha,beta-unsaturated imines, which provided a n ew and useful approach to synthesize allyl amines with good yields and high regioselectivity. Furthermore, for N-chiral alkyl alpha,beta-uns aturated imine, in the case of n-butyl lithium, the diastereoselectivi ty achieved highly 90%. (C) 1997 Elsevier Science S.A.