The addition of allyltrimethylsilane to cyclic N-acyliminium ions derived from(S)-(+)-mandelic acid and cyclohexyl-based chiral auxiliaries

dc.creatorD'Oca, Marcelo G. M.
dc.creatorPilli, Ronaldo A.
dc.creatorPardini, Vera L.
dc.creatorCuri, Denise
dc.creatorComninos, Francisco C. M.
dc.date2001-08-01
dc.date2014-07-17T17:18:02Z
dc.date2015-11-26T11:55:07Z
dc.date2014-07-17T17:18:02Z
dc.date2015-11-26T11:55:07Z
dc.date.accessioned2018-03-28T20:58:11Z
dc.date.available2018-03-28T20:58:11Z
dc.identifierJournal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 12, n. 4, p. 507-513, 2001.
dc.identifier0103-5053
dc.identifierS0103-50532001000400011
dc.identifier10.1590/S0103-50532001000400011
dc.identifierhttp://dx.doi.org/10.1590/S0103-50532001000400011
dc.identifierhttp://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532001000400011
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/25122
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/25122
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1238194
dc.descriptionThe TiCl4- promoted addition of allyltrimethylsilane to chiral 5- and 6-membered N-acyliminium ions employing (S)-(+)-mandelic acid, (1R,2S)-trans-2-phenyl-1-cyclohexanol and (1R,2S,5R)-8-phenylmenthol derivatives as chiral auxiliaries occurred with low to moderate diastereoisomeric ratios (1:1-6:1) to afford 2-substituted amides and carbamates in good yields. The best diastereoselection was observed with (1R,2S,5R)-8-phenylmenthol as the chiral auxiliary. The 2-substituted amides and carbamates were converted to the corresponding alkaloids (S)- and (R)-propyl pyrrolidine and coniine with efficient recovery of the chiral auxiliaries.
dc.descriptionA adição de aliltrimetilsilano, promovida por TiCl4, a íons N-aciliminios cíclicos de 5- e 6-membros derivados do ácido (S)-(+)-mandélico, (1R,2S)-trans-2-fenil-1-cicloexanol e (1R,2S,5R)-8-fenilmentol ocorreu com baixas a moderadas razões diastereoisoméricas (1:1-6:1) e forneceu as respectivas amidas e carbamatos em bons rendimentos. A melhor diastereosseleção facial foi observada com o uso de (1R,2S,5R)-8-fenilmentol como auxiliar quiral. As amidas e carbamatos 2-substituídos foram convertidos nos alcalóides (S)- e (R)-propil pirrolidina e coniina com eficiente recuperação dos auxiliares quirais.
dc.description507
dc.description513
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.languageen
dc.publisherSociedade Brasileira de Química
dc.relationJournal of the Brazilian Chemical Society
dc.rightsaberto
dc.sourceSciELO
dc.subject(S)-(+)-Mandelic acid
dc.subjectcyclohexyl-based chiral auxiliaries
dc.subjectN-acyliminium ions
dc.subjectpyrrolidine and piperidine derivatives
dc.titleThe addition of allyltrimethylsilane to cyclic N-acyliminium ions derived from(S)-(+)-mandelic acid and cyclohexyl-based chiral auxiliaries
dc.typeArtículos de revistas


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