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://repositorio.unifesp.br/handle/11600/3455
http://dx.doi.org/10.1590/S0100-40422007000800036
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 Dias, Luiz C.Aguilar, Andrea Maria [UNIFESP]Universidade Estadual de Campinas (UNICAMP)Universidade Federal de São Paulo (UNIFESP)2015-06-14T13:36:38Z2015-06-14T13:36:38Z2007-01-01Química Nova. Sociedade Brasileira de Química, v. 30, n. 8, p. 2007-2015, 2007.0100-4042http://repositorio.unifesp.br/handle/11600/3455http://dx.doi.org/10.1590/S0100-40422007000800036S0100-40422007000800036.pdfS0100-4042200700080003610.1590/S0100-40422007000800036WOS:000252066900037High 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.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Universidade Estadual de Campinas Instituto de QuímicaUniversidade Federal de São Paulo (UNIFESP)UNIFESP, ICAQFSciELO2007-2015porSociedade Brasileira de QuímicaQuímica Nova1,5-anti inductionboron enolatesaldol reactionsIndução 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 ketonesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UNIFESPinstname:Universidade Federal de São Paulo (UNIFESP)instacron:UNIFESPORIGINALS0100-40422007000800036.pdfapplication/pdf749803${dspace.ui.url}/bitstream/11600/3455/1/S0100-40422007000800036.pdfa94c8edcd84dfaf3276fb819d098f917MD51open accessTEXTS0100-40422007000800036.pdf.txtS0100-40422007000800036.pdf.txtExtracted texttext/plain43756${dspace.ui.url}/bitstream/11600/3455/9/S0100-40422007000800036.pdf.txt3ff963f5863ef268be03a8ddfb688b21MD59open accessTHUMBNAILS0100-40422007000800036.pdf.jpgS0100-40422007000800036.pdf.jpgIM Thumbnailimage/jpeg6706${dspace.ui.url}/bitstream/11600/3455/11/S0100-40422007000800036.pdf.jpg38e52392691fa154c0ba460316878acbMD511open access11600/34552023-06-05 19:21:27.823open accessoai:repositorio.unifesp.br:11600/3455Repositório InstitucionalPUBhttp://www.repositorio.unifesp.br/oai/requestopendoar:34652023-06-05T22:21:27Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)false
dc.title.pt.fl_str_mv Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos
dc.title.alternative.en.fl_str_mv 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.institution.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.eng.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.issued.fl_str_mv 2007-01-01
dc.date.accessioned.fl_str_mv 2015-06-14T13:36:38Z
dc.date.available.fl_str_mv 2015-06-14T13:36:38Z
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dc.identifier.citation.fl_str_mv Química Nova. Sociedade Brasileira de Química, v. 30, n. 8, p. 2007-2015, 2007.
dc.identifier.uri.fl_str_mv http://repositorio.unifesp.br/handle/11600/3455
http://dx.doi.org/10.1590/S0100-40422007000800036
dc.identifier.issn.none.fl_str_mv 0100-4042
dc.identifier.file.none.fl_str_mv S0100-40422007000800036.pdf
dc.identifier.scielo.none.fl_str_mv S0100-40422007000800036
dc.identifier.doi.none.fl_str_mv 10.1590/S0100-40422007000800036
dc.identifier.wos.none.fl_str_mv WOS:000252066900037
identifier_str_mv Química Nova. Sociedade Brasileira de Química, v. 30, n. 8, p. 2007-2015, 2007.
0100-4042
S0100-40422007000800036.pdf
S0100-40422007000800036
10.1590/S0100-40422007000800036
WOS:000252066900037
url http://repositorio.unifesp.br/handle/11600/3455
http://dx.doi.org/10.1590/S0100-40422007000800036
dc.language.iso.fl_str_mv por
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dc.relation.ispartof.none.fl_str_mv Química Nova
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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dc.format.none.fl_str_mv 2007-2015
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)
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institution UNIFESP
reponame_str Repositório Institucional da UNIFESP
collection Repositório Institucional da UNIFESP
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