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|Type:||Artigo de periódico|
|Title:||1,5-asymmetric Induction In Boron-mediated Aldol Reactions Of Beta-oxygenated Methyl Ketones.|
|Author:||Dias, Luiz C|
Aguilar, Andrea M
|Abstract:||This tutorial review describes that high levels of substrate-controlled, 1,5-stereoinduction are obtained in the boron-mediated aldol reactions of beta-oxygenated methyl ketones with achiral and chiral aldehydes. Remote induction from the boron enolates gives the 1,5-anti adducts, with the enolate pi-facial selectivity critically dependent upon the nature of the beta-alkoxy protecting group. This 1,5-anti aldol methodology has been strategically employed in the total synthesis of several natural products with remarkable pharmacological activities. 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 hydrogen bonding between the beta-alkoxy oxygen and the formyl aldehyde hydrogen has recently been proposed.|
|Appears in Collections:||Artigos e Materiais de Revistas Científicas - Unicamp|
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