1,5-asymmetric induction in boron-mediated aldol reactions of beta-oxygenated methyl ketones

dc.contributor.authorDias, Luiz C.
dc.contributor.authorAguilar, Andrea M. [UNIFESP]
dc.contributor.institutionUniversidade Estadual de Campinas (UNICAMP)
dc.contributor.institutionUniversidade Federal de São Paulo (UNIFESP)
dc.date.accessioned2016-01-24T13:49:24Z
dc.date.available2016-01-24T13:49:24Z
dc.date.issued2008-01-01
dc.description.abstractThis 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.en
dc.description.affiliationUniv Estadual Campinas, Inst Quim, BR-13084971 Campinas, SP, Brazil
dc.description.affiliationUniversidade Federal de São Paulo, Dept Ciencias Exatas & Terra, BR-09972270 Diadema, SP, Brazil
dc.description.affiliationUnifespUniversidade Federal de São Paulo, Dept Ciencias Exatas & Terra, BR-09972270 Diadema, SP, Brazil
dc.description.sourceWeb of Science
dc.format.extent451-469
dc.identifierhttp://dx.doi.org/10.1039/b701081h
dc.identifier.citationChemical Society Reviews. Cambridge: Royal Soc Chemistry, v. 37, n. 3, p. 451-469, 2008.
dc.identifier.doi10.1039/b701081h
dc.identifier.issn0306-0012
dc.identifier.urihttp://repositorio.unifesp.br/handle/11600/30304
dc.identifier.wosWOS:000252757500002
dc.language.isoeng
dc.publisherRoyal Soc Chemistry
dc.relation.ispartofChemical Society Reviews
dc.rightsAcesso restrito
dc.title1,5-asymmetric induction in boron-mediated aldol reactions of beta-oxygenated methyl ketonesen
dc.typeResenha
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