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 configur...

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Bibliographic Details
Published in:	Organic letters Vol. 9; no. 21; pp. 4123 - 4126
Main Authors:	Vidal, Paloma, Pedregal, Concepción, Díaz, Nuria, Broughton, Howard, Aceña, José L, Jiménez, Alma, Espinosa, Juan F
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 11-10-2007
Subjects:	Amides - chemistry Magnetic Resonance Spectroscopy Molecular Conformation Molecular Structure Pyrrolidines - chemistry Stereoisomerism
Online Access:	Get full text
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Summary:	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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol701502e