New chiral 3-naphthylaminomethylpyrrolidines: An unexpected epimerisation reaction

Cristiana Fava, Roberta Galeazzi, Giovanna Mobbili, Mario Orena

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)2463-2470
Number of pages8
JournalHeterocycles
Volume51
Issue number10
Publication statusPublished - Oct 1 1999

ASJC Scopus subject areas

  • Organic Chemistry

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