1,5-asymmetric Induction In Boron-mediated Aldol Reactions Of Beta-oxygenated Methyl Ketones.

dc.creatorDias, Luiz C
dc.creatorAguilar, Andrea M
dc.date2008-Mar
dc.date2015-11-27T13:13:35Z
dc.date2015-11-27T13:13:35Z
dc.date.accessioned2018-03-29T01:08:14Z
dc.date.available2018-03-29T01:08:14Z
dc.identifierChemical Society Reviews. v. 37, n. 3, p. 451-69, 2008-Mar.
dc.identifier0306-0012
dc.identifier10.1039/b701081h
dc.identifierhttp://www.ncbi.nlm.nih.gov/pubmed/18224256
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/198167
dc.identifier18224256
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1298400
dc.descriptionThis 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.
dc.description37
dc.description451-69
dc.languageeng
dc.relationChemical Society Reviews
dc.relationChem Soc Rev
dc.rightsaberto
dc.rights
dc.sourcePubMed
dc.subjectAldehydes
dc.subjectBiological Products
dc.subjectBoron
dc.subjectHydrogen Bonding
dc.subjectKetones
dc.subjectStereoisomerism
dc.title1,5-asymmetric Induction In Boron-mediated Aldol Reactions Of Beta-oxygenated Methyl Ketones.
dc.typeArtículos de revistas


Este ítem pertenece a la siguiente institución