« Previous AbstractPositive selection in the ComC-ComD system of Streptococcal Species    Next Abstract"Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using (S)-2-methoxy-2-(1-naphthyl)propionic acid" »

Chirality

Title:		"Stereochemical studies of chiral resolving agents, M9PP and H9PP acids"
Author(s):		Ichikawa A; Ono H; Harada N;
Address:		"National Institute of Agrobiological Sciences, Tsukuba, Ibaraki, Japan. ichikawa@affrc.go.jp"
Journal Title:		Chirality
Year:		2004
Volume:		16
Issue:		8
Page Number:		559 - 567
DOI:		10.1002/chir.20076
ISSN/ISBN:		0899-0042 (Print) 0899-0042 (Linking)
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"
Keywords:		"Chromatography, High Pressure Liquid Esters/*chemistry Hydroxy Acids Magnetic Resonance Spectroscopy Molecular Structure Phenanthrenes/chemical synthesis/*chemistry Propionates/chemical synthesis/*chemistry Stereoisomerism;"
Notes:		"MedlineIchikawa, Akio Ono, Hiroshi Harada, Nobuyuki eng 2004/08/04 Chirality. 2004 Oct; 16(8):559-67. doi: 10.1002/chir.20076"