New chiral 3-naphthylaminomethylpyrrolidines: An unexpected epimerisation reaction

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 forma...

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Bibliographic Details
Published inHeterocycles Vol. 51; no. 10; pp. 2463 - 2470
Main Authors Fava, C, Galeazzi, R, Mobbili, G, Orena, M
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.10.1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC ALDOL REACTION
ACID
ACYLATION
SILYL ENOL ETHERS
MN(III)
ALDEHYDES
NICOTINIC ACETYLCHOLINE-RECEPTORS
CONVENIENT APPROACH
DIAMINE
CYCLIZATION
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Summary: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.
ISSN:0385-5414
DOI:10.3987/com-99-8648