Preparation, characterization and application of a stationary chromatographic phase from a new (+)-tartaric acid derivative

Sacha Legrand (Corresponding Author), Harri Heikkinen, Ian A. Nicholls, Andrew Root, Johan Svenson, C. Rikard Unelius

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)

Abstract

The preparation, characterization and application of a new stationary phase derived from 1,4-cyclohexanedione and diethyl (+)-tartrate are described. A suitable TADDOL for immobilization has been synthesized and grafted to a γ-mercaptopropylsilylated silica gel. The resulting modified stationary phase has been characterized and its ability to separate enantiomers has been studied. While the free TADDOL in solution was able to resolve a range of enantiomers, the resolving properties were lost on immobilization. Solid state 13C CPMAS NMR of the new stationary phase was used to explain the lack of stereoselective recognition.
Original languageEnglish
Pages (from-to)2258-2261
JournalTetrahedron Letters
Volume51
Issue number17
DOIs
Publication statusPublished - 2010
MoE publication typeA1 Journal article-refereed

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Enantiomers
Immobilization
Derivatives
Silica Gel
Nuclear magnetic resonance
tartaric acid
diethyl tartrate
Carbon-13 Magnetic Resonance Spectroscopy
1,4-cyclohexanedione

Cite this

Legrand, Sacha ; Heikkinen, Harri ; Nicholls, Ian A. ; Root, Andrew ; Svenson, Johan ; Unelius, C. Rikard. / Preparation, characterization and application of a stationary chromatographic phase from a new (+)-tartaric acid derivative. In: Tetrahedron Letters. 2010 ; Vol. 51, No. 17. pp. 2258-2261.
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Preparation, characterization and application of a stationary chromatographic phase from a new (+)-tartaric acid derivative. / Legrand, Sacha (Corresponding Author); Heikkinen, Harri; Nicholls, Ian A.; Root, Andrew; Svenson, Johan; Unelius, C. Rikard.

In: Tetrahedron Letters, Vol. 51, No. 17, 2010, p. 2258-2261.

Research output: Contribution to journalArticleScientificpeer-review

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T1 - Preparation, characterization and application of a stationary chromatographic phase from a new (+)-tartaric acid derivative

AU - Legrand, Sacha

AU - Heikkinen, Harri

AU - Nicholls, Ian A.

AU - Root, Andrew

AU - Svenson, Johan

AU - Unelius, C. Rikard

PY - 2010

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AB - The preparation, characterization and application of a new stationary phase derived from 1,4-cyclohexanedione and diethyl (+)-tartrate are described. A suitable TADDOL for immobilization has been synthesized and grafted to a γ-mercaptopropylsilylated silica gel. The resulting modified stationary phase has been characterized and its ability to separate enantiomers has been studied. While the free TADDOL in solution was able to resolve a range of enantiomers, the resolving properties were lost on immobilization. Solid state 13C CPMAS NMR of the new stationary phase was used to explain the lack of stereoselective recognition.

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DO - 10.1016/j.tetlet.2010.02.101

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