Substituent influence on the diastereoselectivity of the alkylation of cyclic chiral imines

Detalhes bibliográficos
Autor(a) principal: Santos, Éverton M. dos
Data de Publicação: 2007
Outros Autores: Bogdan, Marizane, Victor, Maurício Moraes, Tenius, Beatriz S. M., Oliveira, Eduardo R. de
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFBA
Texto Completo: http://www.repositorio.ufba.br/ri/handle/ri/4979
Resumo: p. 370-377,Mar/Apr.
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spelling Santos, Éverton M. dosBogdan, MarizaneVictor, Maurício MoraesTenius, Beatriz S. M.Oliveira, Eduardo R. deSantos, Éverton M. dosBogdan, MarizaneVictor, Maurício MoraesTenius, Beatriz S. M.Oliveira, Eduardo R. de2011-12-22T11:22:13Z2011-12-22T11:22:13Z20070103-5053http://www.repositorio.ufba.br/ri/handle/ri/4979v. 18, n. 2.p. 370-377,Mar/Apr.A alta diastereosseletividade, normalmente observada na reação de alquilação de iminas quirais derivadas de cetonas cíclicas, não é observada no caso de cetonas com substituintes quirais. A influência do tamanho do substituinte foi estudada com iminas preparadas a partir da (5R)-2,5-dimetilciclohexanona e (5R)-carvomentona com ambos enantiômeros da 1-feniletilamina (PEA). Usando metil vinil cetona como eletrófilo, um caso matched foi observado com a imina derivada da (S)-PEA. Entretanto, o ed depende fortemente do substituinte no caso mismatched partindo-se da (R)-PEA. O aumento do volume do substituinte leva à diminuição do ed na ordem iPr– < CH2=C(CH3)– < Me–. Os resultados são explicados pela hipótese de um controle estereoeletrônico a favor de um ataque axial ao tautômero enamina. O equilíbrio conformacional da enamina aparenta ser crucial para explicar os dados experimentais. No caso matched somente um confôrmero é esperado enquanto a mistura dos confôrmeros é postulada no caso mismatched.Submitted by JURANDI DE SOUZA SILVA (jssufba@hotmail.com) on 2011-12-22T11:22:13Z No. of bitstreams: 1 a19v18n2.pdf: 321020 bytes, checksum: be53b41c5a0dad4bafbf624503c2d849 (MD5)Made available in DSpace on 2011-12-22T11:22:13Z (GMT). No. of bitstreams: 1 a19v18n2.pdf: 321020 bytes, checksum: be53b41c5a0dad4bafbf624503c2d849 (MD5) Previous issue date: 2007São Paulohttp://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000200019&lng=en&nrm=isoreponame:Repositório Institucional da UFBAinstname:Universidade Federal da Bahia (UFBA)instacron:UFBAChiral iminesMichael reactionDiastereoselectivitySubstituent influence on the diastereoselectivity of the alkylation of cyclic chiral iminesJournal of the Brazilian Chemical Societyinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleenginfo:eu-repo/semantics/openAccessORIGINALa19v18n2.pdfa19v18n2.pdfapplication/pdf321020https://repositorio.ufba.br/bitstream/ri/4979/1/a19v18n2.pdfbe53b41c5a0dad4bafbf624503c2d849MD51LICENSElicense.txtlicense.txttext/plain1809https://repositorio.ufba.br/bitstream/ri/4979/2/license.txt8bb3e3eb871f5854a9ec419f68651b60MD52TEXTa19v18n2.pdf.txta19v18n2.pdf.txtExtracted texttext/plain30316https://repositorio.ufba.br/bitstream/ri/4979/3/a19v18n2.pdf.txt809c329f5af47ffac38df5885eb2eea7MD53ri/49792022-07-05 14:03:15.694oai:repositorio.ufba.br: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ório InstitucionalPUBhttp://192.188.11.11:8080/oai/requestopendoar:19322022-07-05T17:03:15Repositório Institucional da UFBA - Universidade Federal da Bahia (UFBA)false
dc.title.pt_BR.fl_str_mv Substituent influence on the diastereoselectivity of the alkylation of cyclic chiral imines
dc.title.alternative.pt_BR.fl_str_mv Journal of the Brazilian Chemical Society
title Substituent influence on the diastereoselectivity of the alkylation of cyclic chiral imines
spellingShingle Substituent influence on the diastereoselectivity of the alkylation of cyclic chiral imines
Santos, Éverton M. dos
Chiral imines
Michael reaction
Diastereoselectivity
title_short Substituent influence on the diastereoselectivity of the alkylation of cyclic chiral imines
title_full Substituent influence on the diastereoselectivity of the alkylation of cyclic chiral imines
title_fullStr Substituent influence on the diastereoselectivity of the alkylation of cyclic chiral imines
title_full_unstemmed Substituent influence on the diastereoselectivity of the alkylation of cyclic chiral imines
title_sort Substituent influence on the diastereoselectivity of the alkylation of cyclic chiral imines
author Santos, Éverton M. dos
author_facet Santos, Éverton M. dos
Bogdan, Marizane
Victor, Maurício Moraes
Tenius, Beatriz S. M.
Oliveira, Eduardo R. de
author_role author
author2 Bogdan, Marizane
Victor, Maurício Moraes
Tenius, Beatriz S. M.
Oliveira, Eduardo R. de
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Santos, Éverton M. dos
Bogdan, Marizane
Victor, Maurício Moraes
Tenius, Beatriz S. M.
Oliveira, Eduardo R. de
Santos, Éverton M. dos
Bogdan, Marizane
Victor, Maurício Moraes
Tenius, Beatriz S. M.
Oliveira, Eduardo R. de
dc.subject.por.fl_str_mv Chiral imines
Michael reaction
Diastereoselectivity
topic Chiral imines
Michael reaction
Diastereoselectivity
description p. 370-377,Mar/Apr.
publishDate 2007
dc.date.issued.fl_str_mv 2007
dc.date.accessioned.fl_str_mv 2011-12-22T11:22:13Z
dc.date.available.fl_str_mv 2011-12-22T11:22:13Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://www.repositorio.ufba.br/ri/handle/ri/4979
dc.identifier.issn.none.fl_str_mv 0103-5053
dc.identifier.number.pt_BR.fl_str_mv v. 18, n. 2.
identifier_str_mv 0103-5053
v. 18, n. 2.
url http://www.repositorio.ufba.br/ri/handle/ri/4979
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
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dc.source.none.fl_str_mv reponame:Repositório Institucional da UFBA
instname:Universidade Federal da Bahia (UFBA)
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instname_str Universidade Federal da Bahia (UFBA)
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reponame_str Repositório Institucional da UFBA
collection Repositório Institucional da UFBA
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