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Type: Artigo de periódico
Title: Addition of kinetic boron enolates generated from beta-alkoxy methyl ketones to aldehydes. Density functional theory calculations on the transition structures
Author: Dias, LC
Pinheiro, SM
de Oliveira, VM
Ferreira, MAB
Tormena, CF
Aguilar, AM
Zukerman-Schpector, J
Tiekink, ERT
Abstract: Herein we report that good to excellent levels of 1,5-anti stereoinduction are obtained in boron enolate aldol reactions of 1,2-syn beta-alkoxy methyl ketones with achiral aldehydes, when the beta-alkoxy protecting group is part of a benzylidene acetal. We have also investigated the effects of the ligands on boron, the alpha-, beta-, and gamma-substituents and the beta-alkoxy protecting group on the boron enolates, using density functional theory (B3LYP) and Moller-Plesset perturbation theory (MP2) calculations. (C) 2009 Elsevier Ltd. All rights reserved,
Subject: Aldol reactions
Boron enolates
Theoretical calculations
Natural bond orbital analysis
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Rights: fechado
Identifier DOI: 10.1016/j.tet.2009.08.042
Date Issue: 2009
Appears in Collections:Unicamp - Artigos e Outros Documentos

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