NEW CHIRAL 3-NAPHTHYLAMINOMETHYL-PYRROLIDINES:AN UNEXPECTED EPJIMERISATION REACTION

摘要

New enantiomerically pure 3-naphthylaminomethylpyrrolidines (8),(9),(14) and (15) were obtained through simple steps starting from chiral 4-ethenylpyrrolidin-2-ones (2) and (3).On the other hand,starting rfom pyrrolidine (16),an epimerisation reaction occurred,which was explained through formation of the bicyclic ammonium salt (18).Nucleophilic addition of Et_2Zn to benzaldehyde,carried out in the presence of 8,gave (S)-1-pheny1-1-propanol in 28% e.e.