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

Sacha Legrand; Harri Heikkinen; Ian A. Nicholls; Andrew Root; Johan Svenson; C. Rikard Unelius

doi:10.1016/j.tetlet.2010.02.101

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

Sacha Legrand^*
, Harri Heikkinen
, Ian A. Nicholls
, Andrew Root
, Johan Svenson
, C. Rikard Unelius

^*Corresponding author for this work

VTT Technical Research Centre of Finland

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

8 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 language	English
Pages (from-to)	2258-2261
Journal	Tetrahedron Letters
Volume	51
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2010.02.101
Publication status	Published - 2010
MoE publication type	A1 Journal article-refereed

Access to Document

10.1016/j.tetlet.2010.02.101

Cite this

@article{7a7b6b70f82846c49fc27cb146e6f621,

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

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.",

author = "Sacha Legrand and Harri Heikkinen and Nicholls, \{Ian A.\} and Andrew Root and Johan Svenson and Unelius, \{C. Rikard\}",

year = "2010",

doi = "10.1016/j.tetlet.2010.02.101",

language = "English",

volume = "51",

pages = "2258--2261",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "17",

}

TY - JOUR

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

Y1 - 2010

N2 - 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.

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.

U2 - 10.1016/j.tetlet.2010.02.101

DO - 10.1016/j.tetlet.2010.02.101

M3 - Article

SN - 0040-4039

VL - 51

SP - 2258

EP - 2261

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

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

Abstract

Access to Document

Fingerprint

Cite this