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Type: Artigo de periódico
Title: The Role of beta-Bulky Substituents in Aldol Reactions of Boron Enolates of Methylketones with Aldehydes: Experimental and Theoretical Studies by DFT Analysis
Author: Dias, LC
de Lucca, EC
Ferreira, MAB
Garcia, DC
Tormena, CF
Abstract: In this work, we show the influence of the volume of the beta-substituents on the levels of 1,5-stereoselectivities of aldol reactions of boron enolates generated from beta-alkoxy methylketones with aldehydes. Excellent levels of 1,5-syn stereoinduction were obtained when the beta-protecting group is a silicon ether. This remarkable selectivity is attributed to the volume of the beta-bulky substituent of the corresponding boron enolate. We have investigated a stereochemical model using DFT analysis to rationalize the sense of 1,5-syn stereoselectivities of beta-alkyl-beta-alkoxy methylketones.
Country: EUA
Editor: Amer Chemical Soc
Rights: fechado
Identifier DOI: 10.1021/jo2023119
Date Issue: 2012
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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