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

dc.contributor.authorDias, Luiz C.
dc.contributor.authorAguilar, Andrea Maria [UNIFESP]
dc.contributor.institutionUniversidade Estadual de Campinas (UNICAMP)
dc.contributor.institutionUniversidade Federal de São Paulo (UNIFESP)
dc.date.accessioned2015-06-14T13:36:38Z
dc.date.available2015-06-14T13:36:38Z
dc.date.issued2007-01-01
dc.description.abstractHigh 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.affiliationUniversidade Estadual de Campinas Instituto de Química
dc.description.affiliationUniversidade Federal de São Paulo (UNIFESP)
dc.description.affiliationUnifespUNIFESP, ICAQF
dc.description.provenanceMade available in DSpace on 2015-06-14T13:36:38Z (GMT). No. of bitstreams: 0 Previous issue date: 2007-01-01. Added 1 bitstream(s) on 2015-08-14T21:07:03Z : No. of bitstreams: 1 S0100-40422007000800036.pdf: 749803 bytes, checksum: a94c8edcd84dfaf3276fb819d098f917 (MD5)en
dc.description.sourceSciELO
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.format.extent2007-2015
dc.identifierhttp://dx.doi.org/10.1590/S0100-40422007000800036
dc.identifier.citationQuímica Nova. Sociedade Brasileira de Química, v. 30, n. 8, p. 2007-2015, 2007.
dc.identifier.doi10.1590/S0100-40422007000800036
dc.identifier.fileS0100-40422007000800036.pdf
dc.identifier.issn0100-4042
dc.identifier.scieloS0100-40422007000800036
dc.identifier.urihttp://repositorio.unifesp.br/handle/11600/3455
dc.identifier.wosWOS:000252066900037
dc.language.isopor
dc.publisherSociedade Brasileira de Química
dc.relation.ispartofQuímica Nova
dc.rightsAcesso aberto
dc.subject1,5-anti inductionen
dc.subjectboron enolatesen
dc.subjectaldol reactionsen
dc.titleIndução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídospt
dc.title.alternative1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketonesen
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