Stereoselective Synthesis Of Unsymmetrical β,β-diarylacrylates By A Heck-matsuda Reaction: Versatile Building Blocks For Asymmetric Synthesis Of β,β-diphenylpropanoates, 3-aryl-indole, And 4-aryl-3,4-dihydro-quinolin-2-one And Formal Synthesis Of (-)-indatraline.

dc.creatorTaylor, Jason G
dc.creatorCorreia, Carlos Roque D
dc.date2011-Feb
dc.date2015-11-27T13:22:18Z
dc.date2015-11-27T13:22:18Z
dc.date.accessioned2018-03-29T01:14:37Z
dc.date.available2018-03-29T01:14:37Z
dc.identifierThe Journal Of Organic Chemistry. v. 76, n. 3, p. 857-69, 2011-Feb.
dc.identifier1520-6904
dc.identifier10.1021/jo102134v
dc.identifierhttp://www.ncbi.nlm.nih.gov/pubmed/21241065
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/199816
dc.identifier21241065
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1300049
dc.descriptionβ,β-Disubstituted α,β-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 β,β-diarylacrylate compounds possessing two similar aromatic groups remains a substantial challenge. A simple and convenient stereoselective protocol for the preparation of β,β-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 tetrafluoroborates. 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 β,β-diarylpropanoates in high enantioselectivities. The synthesis of a 3-aryl indole and a chiral 4-aryl-2-quinolone from β,β-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.description857-69
dc.languageeng
dc.relationThe Journal Of Organic Chemistry
dc.relationJ. Org. Chem.
dc.rightsfechado
dc.rights
dc.sourcePubMed
dc.titleStereoselective Synthesis Of Unsymmetrical β,β-diarylacrylates By A Heck-matsuda Reaction: Versatile Building Blocks For Asymmetric Synthesis Of β,β-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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