title: Assignment of absolute configuration on the basis of the conformational effects induced by chiral derivatizing agents: the 2-arylpyrrolidine case.
abstract: A novel approach for determining the absolute configuration of a chiral compound is proposed. The methodology is based on the distinct conformational effects imposed on a chiral substrate by each enantiomer of a chiral derivatizing agent. As a proof of concept, it is shown that the absolute configuration of 2-arylpyrrolidines can easily be determined by inspection of the multiplicity of the NMR signal of the methine proton of the pyrrolidine ring in the corresponding Mosher's amides.
authors: Centro de Investigación Lilly, Avenida de la Industria 30, 28108 Alcobendas, Madrid, Spain. vidal_paloma@lilly.com
authors: Paloma
authors: P
authors: Vidal
authors: Concepción
authors: C
authors: Pedregal
authors: Nuria
authors: N
authors: Díaz
authors: Howard
authors: H
authors: Broughton
authors: José L
authors: JL
authors: Aceña
authors: Alma
authors: A
authors: Jiménez
authors: Juan F
authors: JF
authors: Espinosa
mesh_terms: D000577:Amides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D011759:Pyrrolidines