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Additive and Emergent Catalytic Properties of Dimeric Unnatural Amino Acid Derivatives: Aldol and Conjugate Additions.
de Gracia Retamosa, María; Ruiz-Olalla, Andrea; Agirre, Maddalen; de Cózar, Abel; Bello, Tamara; Cossío, Fernando P.
Afiliación
  • de Gracia Retamosa M; Donostia International Physics Center (DIPC), P° Manuel Lardizabal 4, 20018, Donostia/San Sebastián, Spain.
  • Ruiz-Olalla A; Departamento de Química Orgánica I and Instituto de Innovación, en Química Avanzada (ORFEO-CINQA), University of the Basque Country (UPV/EHU), P° Manuel Lardizabal 3, 20018, Donostia/San Sebastián, Spain.
  • Agirre M; Present address: Departamento de Química Orgánica and Centro de Innovación en Químca Avanzada (ORFEO-CINQA), Instituto de Síntesis Orgánica, Universidad de Alicante, 03080, Alicante, Spain.
  • de Cózar A; Departamento de Química Orgánica I and Instituto de Innovación, en Química Avanzada (ORFEO-CINQA), University of the Basque Country (UPV/EHU), P° Manuel Lardizabal 3, 20018, Donostia/San Sebastián, Spain.
  • Bello T; Departamento de Química Orgánica I and Instituto de Innovación, en Química Avanzada (ORFEO-CINQA), University of the Basque Country (UPV/EHU), P° Manuel Lardizabal 3, 20018, Donostia/San Sebastián, Spain.
  • Cossío FP; Present address: CIC Energigune, Parque Tecnológico de Álava, 01510, Vitoria/Gasteiz, Spain.
Chemistry ; 27(63): 15671-15687, 2021 Nov 11.
Article en En | MEDLINE | ID: mdl-34453455
Different densely substituted L- and D-proline esters were prepared by asymmetric (3+2) cycloaddition reactions catalyzed by conveniently selected EhuPhos chiral ligands. The γ-nitro-2-alkoxycarbonyl pyrrolidines thus obtained in either their endo or exo forms were functionalized and coupled to yield the corresponding γ-dipeptides. The catalytic properties of these latter dimers were examined using aldol and conjugate additions as case studies. When aldol reactions were analyzed, an additive behavior in terms of stereocontrol was observed on going from the monomers to the dimers. In contrast, in the case of the conjugate additions between ketones and nitroalkenes, the monomers did not catalyze this reaction, whereas the different γ-dipeptides promoted the formation of the corresponding Michael adducts. Therefore, in this latter case emergent catalytic properties were observed for these novel γ-dipeptides based on unnatural proline derivatives. Under certain conditions stoichiometric amounts of ketone, acid and nitroalkene), formation of N-acyloxy-2-oxooctahydro-1H-indoles was observed.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Aldehídos / Cetonas Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2021 Tipo del documento: Article País de afiliación: España Pais de publicación: Alemania
Texto completo
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Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Aldehídos / Cetonas Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2021 Tipo del documento: Article País de afiliación: España Pais de publicación: Alemania