Please use this identifier to cite or link to this item:
|Type:||Artigo de periódico|
|Title:||1,5-asymmetric Induction In The Boron-mediated Aldol Reactions Of β-oxygenated Methyl Ketones [indução Assimétrica 1,5-anti Na Adição De Enolatos De Boro De Metilcetonas β-oxigenadas A Aldeídos]|
|Abstract:||High levels of substrate-based 1,5-stereoinduction are obtained in the boron-mediated aldol reactions of β-oxygenated methyl ketones with achiral and chiral aldehydes. Remote induction from the boron enolates gives the 1,5-anti adducts, with the enolate π-facial selectivity critically dependent upon the nature of the β-alkoxy protecting group. This 1,5-anti aldol methodology has been strategically employed in the total synthesis of several natural products. At present, the origin of the high level of 1,5-anti induction obtained with the boron enolates is unclear, although a model based on a hydrogen bonding between the alkoxy oxygen and the formyl hydrogen has been recently proposed.|
|Citationo:||Quimica Nova. , v. 30, n. 8, p. 2007 - 2015, 2007.|
|Appears in Collections:||Artigos e Materiais de Revistas Científicas - Unicamp|
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.