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Type: Artigo de periódico
Title: Influence of beta-Substituents in Aldol Reactions of Boron Enolates of beta-Alkoxy Methylketones
Author: Dias, LC
de Lucca, EC
Ferreira, MAB
Garcia, DC
Tormena, CF
Abstract: Moderate to good levels of substrate-based 1,5-syn-stereocontrol could be achieved in the boron-mediated aldol reactions of beta-tert-butyl methylketones with achiral aldehydes, independent of the nature of the beta-alkoxy protecting group (P = PMB or TBS). The analysis of the relative energies of the transition structures by theoretical calculations using the density functional B3LYP shows relative energies favoring the corresponding OUT-1,5-SYN transition structures, explaining the observed 1,5-syn stereoinduction.
Country: EUA
Editor: Amer Chemical Soc
Rights: fechado
Identifier DOI: 10.1021/ol102303p
Date Issue: 2010
Appears in Collections:Unicamp - Artigos e Outros Documentos

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