New chiral 3-naphthylaminomethylpyrrolidines: An unexpected epimerisation reaction

Cristiana Fava; Roberta Galeazzi; Giovanna Mobbili; Mario Orena

New chiral 3-naphthylaminomethylpyrrolidines: An unexpected epimerisation reaction

Cristiana Fava, Roberta Galeazzi, Giovanna Mobbili, Mario Orena

Istituto Nazionale di Riposo e Cura per Anziani V.E. II

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	2463-2470
Number of pages	8
Journal	Heterocycles
Volume	51
Issue number	10
Publication status	Published - Oct 1 1999

ASJC Scopus subject areas

Organic Chemistry

Cite this

@article{2ccf4050f24a40baa1db49313fa3bfdf,

title = "New chiral 3-naphthylaminomethylpyrrolidines: An unexpected epimerisation reaction",

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.",

author = "Cristiana Fava and Roberta Galeazzi and Giovanna Mobbili and Mario Orena",

year = "1999",

month = oct,

day = "1",

language = "English",

volume = "51",

pages = "2463--2470",

journal = "Heterocycles",

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publisher = "Japan Institute of Heterocyclic Chemistry",

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TY - JOUR

T1 - New chiral 3-naphthylaminomethylpyrrolidines

T2 - An unexpected epimerisation reaction

AU - Fava, Cristiana

AU - Galeazzi, Roberta

AU - Mobbili, Giovanna

AU - Orena, Mario

PY - 1999/10/1

Y1 - 1999/10/1

N2 - 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.

AB - 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.

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M3 - Article

AN - SCOPUS:0033214198

VL - 51

SP - 2463

EP - 2470

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 10

ER -

New chiral 3-naphthylaminomethylpyrrolidines: An unexpected epimerisation reaction

Abstract

ASJC Scopus subject areas

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