120(P-76) 各種NMR溶媒における新Mosher法の有効性(ポスター発表の部)

概要

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Since the modified Mosher's method has been reported by our group, it has become indispensable to the absolute configuration determination of natural compounds. The modified Mosher's method is based on Professor Mosher's idea that MTPA ester takes such a conformation, in which the carbinyl proton, carbonyl oxygen, and trifluoromethyl groups are located on the same plane. During the present work, some MTPA esters were obtained as crystals. Their X-ray crystallography shows that the conformations of the MTPA moieties are the same as the proposed one. Proton NMR spectra of the MTPA esters with variety of functional groups were recorded for deuterochloroform, deuterobenzene, deuteromethanol and deuteropyridine solutions. The experiments revealed that the modified Mosher's method was applicable to most of the compounds in these deutero-solvents. Interestingly, the MTPA esters of two cyclopropane compounds exhibited abnormal Δδ distribution in deuterobenzene. However, they showed normal patterns when the proton NMR spectra were recorded for their deuterochloroform, deuteromethanol, and deuteropyridine solutions.
天然有機化合物討論会の論文
2003-09-01