title: Novel approach to 5-substituted proline derivatives using a silver-catalyzed cyclization as the key step.
abstract: A novel synthetic approach to the synthesis of enantiomerically pure 2,5-disubstituted pyrrolines is described. The methodology involves a Ag-catalyzed 5-endo-dig cyclization of enantiopure aryl-substituted acetylene-containing amino acids. It has also been shown that the obtained pyrrolines can be efficiently transformed into the corresponding saturated 5-aryl-substituted proline derivatives.
authors.affiliation: Radboud University Nijmegen, Institute for Molecules and Materials, Toernooiveld 1, NL-6525 ED Nijmegen, The Netherlands.
authors.forename: Bart C J
authors.initials: BC
authors.lastname: van Esseveldt
authors.forename: Paul W H
authors.initials: PW
authors.lastname: Vervoort
authors.forename: Floris L
authors.initials: FL
authors.lastname: van Delft
authors.forename: Floris P J T
authors.initials: FP
authors.lastname: Rutjes
mesh_terms: D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C499756:RP 66803; D012834:Silver; D011392:Proline