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

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2009-10-17
Autores
Dias, Luiz C.
Pinheiro, Savio M.
Oliveira, Vanda M. de
Ferreira, Marco A. B.
Tormena, Claudio F.
Aguilar, Andrea M. [UNIFESP]
Zukerman-Schpector, Julio
Tiekink, Edward R. T.
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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,
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Tetrahedron. Oxford: Pergamon-Elsevier B.V., v. 65, n. 42, p. 8714-8721, 2009.