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Type: Artigo de periódico
Title: The stereochemistry of the addition of chlorotitanium enolates of N-acyl oxazolidin-2-ones to 5-and 6-membered N-acyliminium ions
Author: Pilli, RA
Bockelmann, MA
Alves, CD
Abstract: The stereoselective addition of chiral and achiral titanium enolates derived from the corresponding N-acyl oxazolidin-2-ones to 5- and 6- membered N-acyliminium ions afforded 2-substituted pyrrolidines in moderate to good diastereoisomeric ratio (5:1 to 14:1) while lower diastereoselection was generally observed in the formation of the corresponding 2-substituted piperidines. The stereochemical outcome was found to be modulated by the nature of the cyclic N-acyliminium ion (5- or 6- membered) and of its carbamate and by the N-acyl group in the enolate precursor. The preferential lk approach seems to be dictated mainly by the minimization of non-bonding interactions between the N-acyl group in the chlorotitanium (IV) enolate and the carbamate and methylene groups in the cyclic N-acyliminium ion.
Subject: oxazolidin-2-ones
titanium (IV) enolates
cyclic N-acyliminium ions
2-substituted pyrrolidines and piperidines
Country: Brasil
Editor: Soc Brasileira Quimica
Citation: Journal Of The Brazilian Chemical Society. Soc Brasileira Quimica, v. 12, n. 5, n. 634, n. 651, 2001.
Rights: aberto
Identifier DOI: 10.1590/S0103-50532001000500007
Date Issue: 2001
Appears in Collections:Unicamp - Artigos e Outros Documentos

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