Assignment of absolute configuration on the basis of the conformational effects induced by chiral derivatizing agents: the 2-arylpyrrolidine case.
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.
Vidal
Paloma
P
Centro de Investigación Lilly, Avenida de la Industria 30, 28108 Alcobendas, Madrid, Spain. vidal_paloma@lilly.com
Pedregal
Concepción
C
Díaz
Nuria
N
Broughton
Howard
H
Aceña
José L
JL
Jiménez
Alma
A
Espinosa
Juan F
JF
D000577:Amides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D011759:Pyrrolidines