Froelich, OlivierDesos, PatriceBonin, MartineQuirion, Jean-CharlesHusson, Henri-PhilippeZhu, Jieping2010-11-252010-11-252010-11-25199610.1021/jo960910shttps://infoscience.epfl.ch/handle/20.500.14299/58560The asym. synthesis of a series of 2-piperidinealkanamines starting from (-)-2-cyano-6-phenyloxazolopiperidine was [i.e., [3R-(3alpha ,5beta ,8abeta )]-hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile] (I) as described. LiAlH4 redn. of I followed by hydrogenolysis gave (-)-2-piperidinemethanamine dihydrochloride (II). Addn. of lithium derivs. to the cyano group of I resulted in the formation of intermediate imino bicyclic systems which could be diastereoselectively reduced to substituted diamino alcs. The addn. of an excess of PhLi to I in the presence of LiBr gave a disubstituted amine, the precursor of diphenyl[(2S)-piperidin-2-yl]methanamine. [on SciFinder (R)]Asymmetric synthesis and induction (asym. synthesis of piperidinealkanamines from (phenyl)oxazolopyridinecarbonitrile)piperidinemethanamine asym synthesis; aminomethyl piperidine asym synthesistext::journal::journal article::research article