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Type: Artigo
Title: Diastereoselectivity in the boron aldol reaction of α-alkoxy and α,β-bis-alkoxy methyl ketones
Author: Fernandes, Alessandra A. G.
Leonarczyk, Ives A.
Ferreira, Marco A. B.
Dias, Luiz Carlos
Abstract: In this work, using DFT calculations, we investigated the 1,4 and 1,5 asymmetric induction in boron enolate aldol reactions of α-alkoxy and α,β-bisalkoxy methyl ketones. We evaluated the steric influence of alkyl substituents at the α position and the stereoelectronic influence of the oxygen protecting groups at the α and β positions. Theoretical calculations revealed the origins of the 1,4 asymmetric induction in terms of the nature of the β-substituent. The synergistic effect between the α,β-syn and α,β-anti-bisalkoxy stereocenters was elucidated. In the presence of the β-alkoxy center, the reaction proceeds through the Goodman–Paton 1,5-stereoinduction model, experiencing a minor influence of the α-alkoxy center
Subject: Energia
Indução assimétrica
Country: Estados Unidos
Editor: Royal Society of Chemistry
Rights: Fechado
Identifier DOI: 10.1039/c9ob00358d
Date Issue: Feb-2019
Appears in Collections:IQ - Artigos e Outros Documentos

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