Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/199837
Type: Artigo de periódico
Title: The Role Of β-bulky Substituents In Aldol Reactions Of Boron Enolates Of Methylketones With Aldehydes: Experimental And Theoretical Studies By Dft Analysis.
Author: Dias, Luiz C
de Lucca, Emílio C
Ferreira, Marco A B
Garcia, Danilo C
Tormena, Cláudio F
Abstract: In this work, we show the influence of the volume of the β-substituents on the levels of 1,5-stereoselectivities of aldol reactions of boron enolates generated from β-alkoxy methylketones with aldehydes. Excellent levels of 1,5-syn stereoinduction were obtained when the β-protecting group is a silicon ether. This remarkable selectivity is attributed to the volume of the β-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 β-alkyl-β-alkoxy methylketones.
Rights: fechado
Identifier DOI: 10.1021/jo2023119
Address: http://www.ncbi.nlm.nih.gov/pubmed/22235771
Date Issue: 2012
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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