1356447-50-1Relevant articles and documents
The role of β-bulky substituents in aldol reactions of boron enolates of methylketones with aldehydes: Experimental and theoretical studies by DFT analysis
Dias, Luiz C.,De Lucca, Emilio C.,Ferreira, Marco A. B.,Garcia, Danilo C.,Tormena, Claudio F.
, p. 1765 - 1788 (2012/04/04)
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.