Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Gas Chromatographic Determination of the Absolute Configuration of Secondary Alcohols and Ketones Having 7-Carboxybicyclo-[2.2.1]heptane Skeleton
Yoshimitsu YAMAZAKIHidekatsu MAEDA
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1986 年 50 巻 1 号 p. 79-87

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Stereoisomers of 7-carboxy- and/or 7-methoxycarbonylbicyclo[2.2.1]heptan-2-ol, heptan-2-one, hept-5-en-2-ol, and hept-5-en-2-one were prepared as the racemic and enantiomerically pure forms. Gas chromatographic enantiomer separation of these compounds was investigated for their diastereomeric derivatives prepared with eight chiral reagents. Among them, (R)-(-)-1-(1-naphthyl)ethyl isocyanate and (R)-(+)-α-methylbenzylamine were the most effective reagents for the hydroxy esters and keto acids, respectively, from the point of complete resolution of the enantiomers on OV-1 capillary columns. The peak components were assigned including the absolute configuration.
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© Japan Society for Bioscience, Biotechnology, and Agrochemistry
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