Assignment of Absolute Configuration on the Basis of the Conformational Effects Induced by Chiral Derivatizing Agents: The 2-Arylpyrrolidine Case
Organic Letters2007Vol. 9(21), pp. 4123–4126
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Paloma Vidal, Concepción Pedregal, Nuria Cirauqui, Howard B. Broughton, José Luis Aceña, Alma Jiménez, Juan F. Espinosa
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.
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