title: Asymmetric synthesis of proline-based conformationally constrained tryptophan mimetic.
abstract: The synthesis of an optically pure proline-based tryptophan mimetic is described. The strategy involves the in situ generation of an unprecedented allylmetal species containing the indole moiety, and its coupling with a chiral imine. The construction of the 3-substituted proline skeleton is then achieved through a hydrozirconation/iodination sequence applied to the resulting homoallylic amine.
authors.affiliation: ICMR, CNRS-UMR 6229, Université de Reims Champagne-Ardenne, BP 1039, 51687, Reims Cedex 2, France.
authors.forename: Pierre-Olivier
authors.initials: PO
authors.lastname: Delaye
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Vasse
authors.forename: Jan
authors.initials: J
authors.lastname: Szymoniak
mesh_terms: D040761:Biomimetic Materials / Q000138:chemical synthesis*; D007455:Iodine / Q000737:chemistry; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
chemical_list: D014364:Tryptophan; D007455:Iodine; D011392:Proline