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Type: Artigo de periódico
Title: Stereoselective alkylation of N-Boc-2-pyrrolidinones and N-Boc-2-piperidinones. Synthesis and characterization of disubstituted lactams
Author: Maldaner, AO
Pilli, RA
Abstract: Alkylation of enolates of monosubstituted N-Boc lactams 4-6 afforded trans-disubstituted lactams as the major isomer. In the pyrrolidinone series, 1,3-induction seems to be ruled by steric interactions and the diastereoselection is low for the alkylation of enolates with small substituents at C-5 (e.g., Me) and methyl iodide. The trans selectivity improves with bulkier substituents at C-2 and/or bulkier electrophiles. The formation of 3,6-trans-disubstituted piperidinones benefits from the axial orientation of the substituent at C-2 due to the A(1,3) strain with the N-Boc group and excellent trans preference is observed even in the alkylation of the lithium enolate of N-Boc-6-methyl piperidinone with methyl iodide. (C) 1999 Elsevier Science ltd. All rights reserved.
Subject: disubstituted pyrrolidinones and piperidinones
steric and stereoelectronic effects
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Citation: Tetrahedron. Pergamon-elsevier Science Ltd, v. 55, n. 47, n. 13321, n. 13332, 1999.
Rights: fechado
Identifier DOI: 10.1016/S0040-4020(99)00835-2
Date Issue: 1999
Appears in Collections:Unicamp - Artigos e Outros Documentos

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