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Type: Artigo de periódico
Title: 1,5-asymmetric induction in the boron-mediated aldol reactions of beta-oxygenated methyl ketones
Author: Dias, LC
Aguilar, AM
Abstract: High levels of substrate-based 1,5-stereoinduction are obtained in the boron-mediated aldol reactions of P-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. 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.
Subject: 1,5-anti induction
boron enolates
aldol reactions
Country: Brasil
Editor: Soc Brasileira Quimica
Citation: Quimica Nova. Soc Brasileira Quimica, v. 30, n. 8, n. 2007, n. 2015, 2007.
Rights: aberto
Identifier DOI: 10.1590/S0100-40422007000800036
Date Issue: 2007
Appears in Collections:Unicamp - Artigos e Outros Documentos

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