title: Diastereo- and enantioselective three-component coupling approach to highly substituted pyrrolidines.
abstract: The enantioselective synthesis of substituted pyrrolidines through a mild Lewis-acid catalyzed three-component coupling reaction between picolinaldehyde, amino acids, and activated olefins is reported. The reaction uses low catalyst loadings of commercially available chiral diamines and copper triflate proposed to self-assemble in conjunction with the chelating aldehydes, 4-substituted-2-picolinaldehydes or 4-methylthiazole-2-carboxaldehyde, to generate a catalyst complex. A model is provided to explain how this complex directs enantioselectivity. This work represents a significant advance in the ease, scope, and cost of producing highly substituted, enantioenriched pyrrolidines.
authors: Department of Chemistry, Indiana University , 800 E. Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States.
authors: Mani Raj
authors: MR
authors: Chaulagain
authors: Albert E
authors: AE
authors: Felten
authors: Kevin
authors: K
authors: Gilbert
authors: Zachary D
authors: ZD
authors: Aron
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000596:Amino Acids; D011725:Pyridines; D011759:Pyrrolidines; C522921:picolinaldehyde