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Note | Regular issue | Vol 51, No. 10, 1999, pp.2463-2470
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8648
New Chiral 3-Naphthylaminomethylpyrroli- dines: An Unexpected Epimerisation Reaction

Cristiana Fava, Roberta Galeazzi, Giovanna Mobbili, and Mario Orena*

*Dipartimento di Scienze dei Materiali e della Terra, Università di Ancona, Via Brecce Bianche, I-60131 Ancona, Italy


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 from pyrrolidine (16), an epimerisation reaction occurred, which was explained through formation of the bicyclic ammonium salt (18). Nucleophilic addition of Et2Zn to benzaldehyde, carried out in the presence of 8, gave (S)-1-phenyl-1-propanol in 28% e.e.