A Chiral Bis(arsine) Ligand: synthesis and applications in Palladium catalyzed asymmetric Allylic Alkylations

dc.creatorUberman, Paula Marina
dc.creatorCaira, Mino R.
dc.creatorMartín, Sandra Elizabeth
dc.date2013-05
dc.identifierhttp://hdl.handle.net/11336/25413
dc.identifierUberman, Paula Marina; Caira, Mino R.; Martín, Sandra Elizabeth; A Chiral Bis(arsine) Ligand: synthesis and applications in Palladium catalyzed asymmetric Allylic Alkylations; American Chemical Society; Organometallics; 32; 11; 5-2013; 3220-3226
dc.identifier0276-7333
dc.identifierCONICET Digital
dc.identifierCONICET
dc.descriptionThe new chiral bis(arsine) ligand N,N′-bis[2′- (diphenylarsino)benzoyl]-(1R,2R)-cyclohexanediamine (BiAsBA, 3), based on the backbone of the Trost modular ligand (TML), was synthesized in three steps. A useful approach to introduce the −AsPh2 group on arsine ligands by Pd-catalyzed arsination was used. The molecular structure and configuration of the BiAsBA ligand was determined by single-crystal X-ray crystallography. In the asymmetric allylic alkylation of 1,3-diphenyl-2- propenyl acetate with dimethyl malonate very high to complete conversion and modest enantioselectivity were achieved. Despite the low enantioselectivity obtained, the bis(arsine) ligand BiAsBA showed significant potential, since it provided a higher ee value than the phosphorus-containing homologous “Trost standard ligand” (TSL) with the same substrate.
dc.descriptionFil: Uberman, Paula Marina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
dc.descriptionFil: Caira, Mino R.. University of Cape Town; Sudáfrica
dc.descriptionFil: Martín, Sandra Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
dc.formatapplication/pdf
dc.formatapplication/pdf
dc.languageeng
dc.publisherAmerican Chemical Society
dc.relationinfo:eu-repo/semantics/altIdentifier/doi/10.1021/om400144s
dc.relationinfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/om400144s
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rightshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subjectArsine Chiral Ligand
dc.subjectAsymmetric Allylic Alkylation
dc.subjectPalladium
dc.subjectCatalyzed Arsination
dc.subjecthttps://purl.org/becyt/ford/1.4
dc.subjecthttps://purl.org/becyt/ford/1
dc.titleA Chiral Bis(arsine) Ligand: synthesis and applications in Palladium catalyzed asymmetric Allylic Alkylations
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:ar-repo/semantics/artículo
dc.typeinfo:eu-repo/semantics/publishedVersion


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