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Stereochemical Studies of Chiral Resolving Agents, M9PP and H9PP Acids

Stereochemical Studies of Chiral Resolving Agents, M9PP and H9PP Acids

Akio Ichikawa, Hiroshi Ono, Nobuyuki Harada

Chirality. 2004 Oct;16(8):559-67.

PMID: 15290692

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP71112646	9-Phenanthrylmagnesium bromide		71112-64-6	Price

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