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

Paul A. Gugger; David C.R. Hockless; Nathan L. Kilah; Renuka C. Mayadunne; S. Bruce Wild

doi:10.1016/j.tetasy.2008.07.018

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

Paul A. Gugger, David C.R. Hockless, Nathan L. Kilah, Renuka C. Mayadunne, S. Bruce Wild^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1810-1812
Number of pages	3
Journal	Tetrahedron Asymmetry
Volume	19
Issue number	15
DOIs	https://doi.org/10.1016/j.tetasy.2008.07.018
Publication status	Published - 8 Aug 2008

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10.1016/j.tetasy.2008.07.018

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@article{37af7ca8071c401c9fc146713cf23000,

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

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.",

author = "Gugger, {Paul A.} and Hockless, {David C.R.} and Kilah, {Nathan L.} and Mayadunne, {Renuka C.} and Wild, {S. Bruce}",

year = "2008",

month = aug,

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doi = "10.1016/j.tetasy.2008.07.018",

language = "English",

volume = "19",

pages = "1810--1812",

journal = "Tetrahedron Asymmetry",

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publisher = "Elsevier Ltd.",

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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. / Gugger, Paul A.; Hockless, David C.R.; Kilah, Nathan L. et al.
In: Tetrahedron Asymmetry, Vol. 19, No. 15, 08.08.2008, p. 1810-1812.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Resolution of (±)-nipecotic acid ((±)-3-piperidinecarboxylic acid) by separation of palladium(II) diastereomers containing orthometallated (S)-(-)-1-[1-(dimethylamino)ethyl]naphthalene

AU - Gugger, Paul A.

AU - Hockless, David C.R.

AU - Kilah, Nathan L.

AU - Mayadunne, Renuka C.

AU - Wild, S. Bruce

PY - 2008/8/8

Y1 - 2008/8/8

N2 - 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.

AB - 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.

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U2 - 10.1016/j.tetasy.2008.07.018

DO - 10.1016/j.tetasy.2008.07.018

M3 - Article

SN - 0957-4166

VL - 19

SP - 1810

EP - 1812

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 15

ER -

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

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