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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 L.C.
De Lucca E.C.
Ferreira M.A.B.
Garcia D.C.
Tormena C.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. © 2012 American Chemical Society.
Citation: Journal Of Organic Chemistry. , v. 77, n. 4, p. 1765 - 1788, 2012.
Rights: fechado
Identifier DOI: 10.1021/jo2023119
Date Issue: 2012
Appears in Collections:Unicamp - Artigos e Outros Documentos

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