Novel Potential Enantioselective Phase Transfer Catalysts Based on Lupinine

Ten N-alkylated lupininium derivatives 5–8 were prepared as potential enantioselective phase transfer catalysts. Compounds 5a–d , 6a–d contain four asymmetric centers (including one in the side chain) with known configuration resting on an X-ray structure. Preliminary PT catalytic experiments in several reactions gave high chemical yields but relatively disappointing enantioselectivities.