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Resolution of (±)-nipecotic acid ((±)-3-piperidinecarboxylic acid) by separation of palladium(II) diastereomers containing orthometallated (S)-(-)-1-[1-(dimethylamino)ethyl]naphthalene

Citation

Gugger, PA and Hockless, DCR and Kilah, NL and Mayadunne, RC and Wild, SB, Resolution of (±)-nipecotic acid ((±)-3-piperidinecarboxylic acid) by separation of palladium(II) diastereomers containing orthometallated (S)-(-)-1-[1-(dimethylamino)ethyl]naphthalene, Tetrahedron: Asymmetry, 19, (15) pp. 1810-1812. ISSN 0957-4166 (2008) [Refereed Article]

Copyright Statement

Copyright 2008 Elsevier Ltd.

DOI: doi:10.1016/j.tetasy.2008.07.018

Abstract

An efficient resolution of ()-nipecotic acid has been achieved by the fractional crystallization of internally diastereomeric palladium(II) complexes containing the chelated carboxylate and orthometallated (S)-()-1-[1-(dimethylamino)ethyl]naphthalene. The configurationally pure enantiomers of the acid were recovered from the individual diastereomers of the complex by treatment with hydrochloric acid, which also regenerated the palladium(II) resolving agent. The crystal structure of the less-soluble diastereomer of the complex has been determined.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Inorganic Chemistry
Research Field:Transition Metal Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Kilah, NL (Dr Nathan Kilah)
ID Code:84267
Year Published:2008
Web of Science® Times Cited:6
Deposited By:Chemistry
Deposited On:2013-05-01
Last Modified:2013-05-08
Downloads:0

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