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

Detalhes bibliográficos
Autor(a) principal: Dias, Luiz C.
Data de Publicação: 2007
Outros Autores: Aguilar, Andrea Maria [UNIFESP]
Tipo de documento: Artigo
Idioma: por
Título da fonte: Repositório Institucional da UNIFESP
Texto Completo: http://dx.doi.org/10.1590/S0100-40422007000800036
http://repositorio.unifesp.br/handle/11600/3455
Resumo: 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.
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spelling Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketones1,5-anti inductionboron enolatesaldol reactionsHigh 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.Universidade Estadual de Campinas Instituto de QuímicaUniversidade Federal de São Paulo (UNIFESP)UNIFESP, ICAQFSciELOFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Sociedade Brasileira de QuímicaUniversidade Estadual de Campinas (UNICAMP)Universidade Federal de São Paulo (UNIFESP)Dias, Luiz C.Aguilar, Andrea Maria [UNIFESP]2015-06-14T13:36:38Z2015-06-14T13:36:38Z2007-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion2007-2015application/pdfhttp://dx.doi.org/10.1590/S0100-40422007000800036Química Nova. Sociedade Brasileira de Química, v. 30, n. 8, p. 2007-2015, 2007.10.1590/S0100-40422007000800036S0100-40422007000800036.pdf0100-4042S0100-40422007000800036http://repositorio.unifesp.br/handle/11600/3455WOS:000252066900037porQuímica Novainfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UNIFESPinstname:Universidade Federal de São Paulo (UNIFESP)instacron:UNIFESP2024-08-05T21:38:46Zoai:repositorio.unifesp.br/:11600/3455Repositório InstitucionalPUBhttp://www.repositorio.unifesp.br/oai/requestbiblioteca.csp@unifesp.bropendoar:34652024-08-05T21:38:46Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)false
dc.title.none.fl_str_mv Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos
1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketones
title Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos
spellingShingle Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos
Dias, Luiz C.
1,5-anti induction
boron enolates
aldol reactions
title_short Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos
title_full Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos
title_fullStr Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos
title_full_unstemmed Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos
title_sort Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos
author Dias, Luiz C.
author_facet Dias, Luiz C.
Aguilar, Andrea Maria [UNIFESP]
author_role author
author2 Aguilar, Andrea Maria [UNIFESP]
author2_role author
dc.contributor.none.fl_str_mv Universidade Estadual de Campinas (UNICAMP)
Universidade Federal de São Paulo (UNIFESP)
dc.contributor.author.fl_str_mv Dias, Luiz C.
Aguilar, Andrea Maria [UNIFESP]
dc.subject.por.fl_str_mv 1,5-anti induction
boron enolates
aldol reactions
topic 1,5-anti induction
boron enolates
aldol reactions
description 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.
publishDate 2007
dc.date.none.fl_str_mv 2007-01-01
2015-06-14T13:36:38Z
2015-06-14T13:36:38Z
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.1590/S0100-40422007000800036
Química Nova. Sociedade Brasileira de Química, v. 30, n. 8, p. 2007-2015, 2007.
10.1590/S0100-40422007000800036
S0100-40422007000800036.pdf
0100-4042
S0100-40422007000800036
http://repositorio.unifesp.br/handle/11600/3455
WOS:000252066900037
url http://dx.doi.org/10.1590/S0100-40422007000800036
http://repositorio.unifesp.br/handle/11600/3455
identifier_str_mv Química Nova. Sociedade Brasileira de Química, v. 30, n. 8, p. 2007-2015, 2007.
10.1590/S0100-40422007000800036
S0100-40422007000800036.pdf
0100-4042
S0100-40422007000800036
WOS:000252066900037
dc.language.iso.fl_str_mv por
language por
dc.relation.none.fl_str_mv Química Nova
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 2007-2015
application/pdf
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv reponame:Repositório Institucional da UNIFESP
instname:Universidade Federal de São Paulo (UNIFESP)
instacron:UNIFESP
instname_str Universidade Federal de São Paulo (UNIFESP)
instacron_str UNIFESP
institution UNIFESP
reponame_str Repositório Institucional da UNIFESP
collection Repositório Institucional da UNIFESP
repository.name.fl_str_mv Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)
repository.mail.fl_str_mv biblioteca.csp@unifesp.br
_version_ 1814268293451612160

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