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Enantioselective Synthesis of α-Amidoboronates Catalyzed by Planar-Chiral NHC-Cu(I) Complexes.
Schwamb, C Benjamin; Fitzpatrick, Keegan P; Brueckner, Alexander C; Richardson, H Camille; Cheong, Paul H-Y; Scheidt, Karl A.
Afiliación
  • Schwamb CB; Department of Chemistry, Center for Molecular Innovation and Drug Discovery , Northwestern University , Silverman Hall , Evanston , Illinois 60208 , United States.
  • Fitzpatrick KP; Department of Chemistry, Center for Molecular Innovation and Drug Discovery , Northwestern University , Silverman Hall , Evanston , Illinois 60208 , United States.
  • Brueckner AC; Department of Chemistry , Oregon State University , 153 Gilbert Hall , Corvallis , Oregon 97331 , United States.
  • Richardson HC; Department of Chemistry , Oregon State University , 153 Gilbert Hall , Corvallis , Oregon 97331 , United States.
  • Cheong PH; Department of Chemistry , Oregon State University , 153 Gilbert Hall , Corvallis , Oregon 97331 , United States.
  • Scheidt KA; Department of Chemistry, Center for Molecular Innovation and Drug Discovery , Northwestern University , Silverman Hall , Evanston , Illinois 60208 , United States.
J Am Chem Soc ; 140(34): 10644-10648, 2018 08 29.
Article en En | MEDLINE | ID: mdl-30102526
ABSTRACT
The first highly selective catalytic hydroboration of alkyl-substituted aldimines to provide medicinally relevant α-amidoboronates is disclosed. The Cu(I)-catalyzed borylation proceeds with excellent facial selectivity when a set of planar-chiral N-heterocyclic carbenes (NHCs) were employed as ligands. Density functional theory computations suggest that interactions between BPin and the planar-chiral catalyst are responsible for the observed stereoselectivity. Important pharmacophores, such as the boronate analogue of isoleucine, can be prepared using a chromatography-free protocol starting from commercially available reagents. The application of these NHC ligands in these Cu(I)-catalyzed processes offers a significant contribution to existing strategies for laboratory-scale preparation of enantioenriched α-amidoboronates.

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2018 Tipo del documento: Article País de afiliación: Estados Unidos

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2018 Tipo del documento: Article País de afiliación: Estados Unidos