24 ジアステオマー法の"本質的問題点"をも解決した超高感度不斉識別法(口頭発表の部)

概要

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Since the discovery of "Enantiomerism" by Louis Pasteur in 18481[1], chiral discrimination has been one of the major subjects in science. However, the most widely used diastereomer method for chiral discrimination an "intrinsic problem" that it is very difficult or impossible to discriminate the diastereomers having chiral centers separated more than four bonds. In order to discriminate such diastereomers, we have proposed a new concept that the chirality of the chiral deriving reagent in the diastereomer provides the diastereomer with a specific preferred chiral conformation and the other chirality in the diastereomer could be discriminated as the chirality directly attached to the chiral molecules. Based on the concept developed we have developed highly potent chiral deriving reagents; 1-(anthracene-2,3-dicarboximido)-2-propyl-OTf, 2-(anthracene-2,3-dicarboximido)-1-propyl-OTf, and 2-(anthracene-2,3-dicarboximido)cyclohexanol for chiral carboxylic aids, and 2-(anthracene-2,3-dicarboximido)cyclohexane carboxylic acid for chiral alcohols[2]. These reagents gave us a solution of the "intrinsic problem" of diastereomer method [3,4] and opened the door to a new chiral discrimination world. The new concept, design of the reagents, abilities of these reagents, and several examples of the determination of the absolute configuration of natural products[5] by use of them will be presented.
2003-09-01