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

Show simple item record Dias, Luiz C. Aguilar, Andrea Maria [UNIFESP] 2015-06-14T13:36:38Z 2015-06-14T13:36:38Z 2007-01-01
dc.identifier.citation Química Nova. Sociedade Brasileira de Química, v. 30, n. 8, p. 2007-2015, 2007.
dc.identifier.issn 0100-4042
dc.description.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. en
dc.description.sponsorship Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorship Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.format.extent 2007-2015
dc.language.iso por
dc.publisher Sociedade Brasileira de Química
dc.relation.ispartof Química Nova
dc.rights Acesso aberto
dc.subject 1,5-anti induction en
dc.subject boron enolates en
dc.subject aldol reactions en
dc.title Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos pt
dc.title.alternative 1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketones en
dc.type Artigo
dc.contributor.institution Universidade Estadual de Campinas (UNICAMP)
dc.contributor.institution Universidade Federal de São Paulo (UNIFESP)
dc.description.affiliation Universidade Estadual de Campinas Instituto de Química
dc.description.affiliation Universidade Federal de São Paulo (UNIFESP)
dc.description.affiliationUnifesp UNIFESP
dc.identifier.file S0100-40422007000800036.pdf
dc.identifier.scielo S0100-40422007000800036
dc.identifier.doi 10.1590/S0100-40422007000800036
dc.description.source SciELO
dc.identifier.wos WOS:000252066900037


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