Stereoselective Synthesis of Unsymmetrical beta,beta-Diarylacrylates by a Heck-Matsuda Reaction: Versatile Building Blocks for Asymmetric Synthesis of beta,beta-Diphenylpropanoates, 3-Aryl-indole, and 4-Aryl-3,4-dihydro-quinolin-2-one and Formal Synthesis of (-)-Indatraline

dc.creatorTaylor, JG
dc.creatorCorreia, CRD
dc.date2011
dc.dateFEB 4
dc.date2014-07-30T13:38:31Z
dc.date2015-11-26T18:06:09Z
dc.date2014-07-30T13:38:31Z
dc.date2015-11-26T18:06:09Z
dc.date.accessioned2018-03-29T00:48:22Z
dc.date.available2018-03-29T00:48:22Z
dc.identifierJournal Of Organic Chemistry. Amer Chemical Soc, v. 76, n. 3, n. 857, n. 869, 2011.
dc.identifier0022-3263
dc.identifierWOS:000286577400013
dc.identifier10.1021/jo102134v
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/52409
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/52409
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1293291
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionbeta,beta-Disubstituted alpha,beta-unsaturated esters may serve as valuable derivatives for the preparation of other highly functionalized systems found in many natural products and marketed drugs. The stereoselective synthesis of unsymmetrical beta,beta-diarylacrylate compounds possessing two similar aromatic groups remains a substantial challenge. A simple and convenient stereoselective protocol for the preparation of beta,beta-disubstituted acrylates via a Heck-Matsuda reaction is reported. Good to high yields were accomplished by a "ligand-free" Pd-catalyzed arylation reaction of cinnamate esters with arenediazonium tetrafluorborates. Both electron-deficient and electron-rich arenediazonium salts could be employed as arylating reagents, and cinnamate esters were generally more reactive when substituted with an electron-donating group. The overall methodology is highly stereoselective, and this attribute was taken advantage of in the asymmetric Cu-catalyzed 1,4 reduction reaction to provide beta,beta-diarylpropanoates in high enantioselectivities. The synthesis of a 3-aryl indole and a chiral 4-aryl-2-quinolone from beta,beta-diarylacrylates was achieved by cyclization in the presence of a diphosphine ligated CuH catalyst. A convenient route for the asymmetric formal synthesis of the psychoactive compound (-)-Indatraline is also presented.
dc.description76
dc.description3
dc.description857
dc.description869
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.languageen
dc.publisherAmer Chemical Soc
dc.publisherWashington
dc.publisherEUA
dc.relationJournal Of Organic Chemistry
dc.relationJ. Org. Chem.
dc.rightsfechado
dc.sourceWeb of Science
dc.subjectAlpha,beta-unsaturated Carbonyl-compounds
dc.subjectConjugate Reduction
dc.subjectArenediazonium Salts
dc.subjectDiazonium Salts
dc.subjectNeurochemical Profile
dc.subjectTransition-metals
dc.subjectArylboronic Acids
dc.subjectMichael Additions
dc.subjectPotent Inhibitor
dc.subjectCopper Hydride
dc.titleStereoselective Synthesis of Unsymmetrical beta,beta-Diarylacrylates by a Heck-Matsuda Reaction: Versatile Building Blocks for Asymmetric Synthesis of beta,beta-Diphenylpropanoates, 3-Aryl-indole, and 4-Aryl-3,4-dihydro-quinolin-2-one and Formal Synthesis of (-)-Indatraline
dc.typeArtículos de revistas


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