Artículos de revistas
Addition of kinetic boron enolates generated from beta-alkoxy methyl ketones to aldehydes. Density functional theory calculations on the transition structures
Registro en:
Tetrahedron. Pergamon-elsevier Science Ltd, v. 65, n. 42, n. 8714, n. 8721, 2009.
0040-4020
WOS:000270611500010
10.1016/j.tet.2009.08.042
Autor
Dias, LC
Pinheiro, SM
de Oliveira, VM
Ferreira, MAB
Tormena, CF
Aguilar, AM
Zukerman-Schpector, J
Tiekink, ERT
Institución
Resumen
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) 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, 65 42 8714 8721 FAEP-UNICAMP Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) CNPq [573.564/2008-6]