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Updated: Aug 23, 2026

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
Published on: August 18, 2017
Stereochemical studies of chiral resolving agents, M9PP and H9PP acids
Akio Ichikawa1, Hiroshi Ono, Nobuyuki Harada
1National Institute of Agrobiological Sciences, Tsukuba, Ibaraki, Japan. ichikawa@affrc.go.jp
Abstract:
The stereoselective Grignard reaction of (1R,2S,5R)-(-)-2-isopropyl-5-methylcyclohexyl pyruvate (menthyl pyruvate) with 9-phenanthrylmagnesium bromide yielded diastereomeric hydroxy-esters, where intramolecular OH em leader O=C hydrogen bond was observed in IR and (1)H NMR spectra. The alkaline hydrolysis of the major product gave (+)-2-hydroxy-2-(9-phenanthryl)propionic acid (H9PP acid (3)), whose absolute configuration was assigned as S based on the chemical correlation with (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester of (S)-2-methoxy-2-(9-phenanthryl)propionic acid (M9PP acid (2)); the absolute configuration of 2 had been previously established by X-ray crystallography. The enantioresolution of (+/-)-6-methyl-5-hepten-2-ol, sulcatol, an insect pheromone, was carried out using (S)-(+)-M9PP acid 2.
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