Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos

Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos

Alternative title 1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketones
Author Dias, Luiz C. Google Scholar
Aguilar, Andrea Maria Autor UNIFESP Google Scholar
Institution Universidade Estadual de Campinas (UNICAMP)
Universidade Federal de São Paulo (UNIFESP)
Abstract High levels of substrate-based 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. 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.
Keywords 1,5-anti induction
boron enolates
aldol reactions
Language Portuguese
Sponsor Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
Date 2007-01-01
Published in Química Nova. Sociedade Brasileira de Química, v. 30, n. 8, p. 2007-2015, 2007.
ISSN 0100-4042 (Sherpa/Romeo, impact factor)
Publisher Sociedade Brasileira de Química
Extent 2007-2015
Origin http://dx.doi.org/10.1590/S0100-40422007000800036
Access rights Open access Open Access
Type Article
Web of Science ID WOS:000252066900037
SciELO ID S0100-40422007000800036 (statistics in SciELO)
URI http://repositorio.unifesp.br/handle/11600/3455

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