Addition of kinetic boron enolates generated from beta-alkoxy methyl ketones to aldehydes. Density functional theory calculations on the transition structures

Addition of kinetic boron enolates generated from beta-alkoxy methyl ketones to aldehydes. Density functional theory calculations on the transition structures

Author Dias, Luiz C. Google Scholar
Pinheiro, Savio M. Google Scholar
Oliveira, Vanda M. de Google Scholar
Ferreira, Marco A. B. Google Scholar
Tormena, Claudio F. Google Scholar
Aguilar, Andrea M. Autor UNIFESP Google Scholar
Zukerman-Schpector, Julio Google Scholar
Tiekink, Edward R. T. Google Scholar
Institution Universidade Estadual de Campinas (UNICAMP)
Universidade Federal de São Paulo (UNIFESP)
Universidade Federal de São Carlos (UFSCar)
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 B.V. All rights reserved,
Keywords Aldol reactions
Boron enolates
Theoretical calculations
Natural bond orbital analysis
1,5-Stereoinduction
Language English
Sponsor FAEP-UNICAMP
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
Grant number CNPq: 573.564/2008-6
Date 2009-10-17
Published in Tetrahedron. Oxford: Pergamon-Elsevier B.V., v. 65, n. 42, p. 8714-8721, 2009.
ISSN 0040-4020 (Sherpa/Romeo, impact factor)
Publisher Elsevier B.V.
Extent 8714-8721
Origin http://dx.doi.org/10.1016/j.tet.2009.08.042
Access rights Closed access
Type Article
Web of Science ID WOS:000270611500010
URI http://repositorio.unifesp.br/handle/11600/31888

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