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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|
de Lucca, EC
|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.|
|Editor:||Amer Chemical Soc|
|Appears in Collections:||Artigos e Materiais de Revistas Científicas - Unicamp|
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