Determination of the enantiomeric purity of compound chiral by virtue of C-13 labelling

Pirkle, William H.; Pavlin, Mark S.

doi:10.1039/c39740000274

Cited by 9 publications

(2 citation statements)

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“…Pirkle continued to study NMR enantiodifferentiation in a chiral environment brought about by the addition of enantioenriched solvating agents. He developed a number of CSAs, the best known of which was 9‐anthryl trifluoromethyl carbinol or Pirkle's alcohol, which was widely used for the NMR determination of enantiopurity of chiral amines, sulfoxides, amino acids, lactones, and other analytes 7 . The enantiopure Pirkle alcohol was sold by Aldrich and supplied by the Pirkle group.…”

Section: Background and Early Yearsmentioning

confidence: 99%

“…He developed a number of CSAs, the best known of which was 9-anthryl trifluoromethyl carbinol or Pirkle's alcohol, which was widely used for the NMR determination of enantiopurity of chiral amines, sulfoxides, amino acids, lactones, and other analytes. 7 The enantiopure Pirkle alcohol was sold by Aldrich and supplied by the Pirkle group. Production of "9 AC" as we called it became a rite of passage for new members of the Pirkle Zoo, exposing them, often for the first time, to organic synthesis on the kilogram scale and the complexities of large-scale preparation of highly…”

Section: Background and Early Yearsmentioning

confidence: 99%

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William H. Pirkle: Stereochemistry pioneer

Welch¹

2020

Chirality

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Professor William H. Pirkle (1934–2018) made a profound impact on modern chemistry by inventing and popularizing widely used techniques for the analysis and purification of enantiomers, contributions that paved the way for the subsequent advances in the discovery, development, and manufacture of enantiopure pharmaceuticals, agrochemicals, and specialty chemicals. Pirkle's pioneering 1966 demonstration of the use of chiral solvating agents for the nuclear magnetic resonance determination of enantiopurity led to a lifelong interest in understanding the supramolecular interactions responsible for enantiodifferentiation. Ongoing research into the chromatographic resolution of stereoisomers throughout the 1970s led in 1981 to the very first commercialization of a chiral stationary phase for the high‐performance liquid chromatography (HPLC) separation of enantiomers. The availability of this and subsequent “Pirkle columns” had a deep and lasting impact, becoming widely embraced by the chemical sciences research community worldwide and spearheading the wholesale changeover to HPLC as the preferred technique for measuring enantiopurity. Doc Pirkle was a highly creative, independent, and fun‐loving collaborator whose circle of friends extends around the globe. His research group at the University of Illinois, often referred to as The Pirkle Zoo, became a refuge for an interesting assembly of characters who flourished under his mentorship and guidance.

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Section: Background and Early Yearsmentioning

confidence: 99%

Section: Background and Early Yearsmentioning

confidence: 99%