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Type: Artigo de periódico
Title: The stereochemistry of the addition of titanium enolates of N-propionyl-oxazolidin-2-ones to 5- and 6-membered N-acyliminium ions
Author: Pilli, RA
Alves, CD
Bockelmann, MA
Mascarenhas, YP
Nery, JG
Vencato, I
Abstract: The stereochemistry of the addition of the N-propionyl titanium enolates 2a and 2b to 5- and 6-membered 2-ethoxycarbamates 1a-f was investigated. The addition proceeded stereoselectively to afford the corresponding (2S,1'S)-2-substituted pyrrolidines as the major diastereoisomer. Despite the lack of reactivity between 2-ethoxypiperidine 1b and N-propionyl titanium enolates 2a and 2b, less bulky carbamate groups on 2-ethoxypiperidines 1d and 1f restored reactivity and the corresponding 2-substituted piperidines were obtained in moderate to good yields although with poor diastereoselection (C) 1999 Elsevier Science Ltd. All rights reserved.
Subject: titanium enolates
N-acyliminium ion
2-substituted pyrrolidines and piperidine
beta-amino acid derivatives
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Rights: fechado
Identifier DOI: 10.1016/S0040-4039(99)00398-6
Date Issue: 1999
Appears in Collections:Unicamp - Artigos e Outros Documentos

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