73(P55) ジフルオロジニトロベンゼンを用いた二級アルコール絶対配置決定法(ポスター発表の部)

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In the present study, we have established a versatile method for the determination of the absolute configurations of the α-carbon of secondary alcohols using the characteristic functions of 1,5-difluoro-2,4-dinitrobenzene (FFDNB) by NMR spectroscopy and HPLC. analysis. In the NMR spectral method, a secondary alcohol reacted first with FFDNB under mild basic conditions and 1-phenyethylamine (PEA) was then introduced into the secondary alcohol-FDNB derivative for the recognition. Because the conformation of the resulting alcohol-DPEA derivative is definitely fixed by the characteristic hydrogen bonding and arrangement of related functional groups, the Δδ values obtained by this method are larger than those by the conventional methods such as modified Mosher method. Additionally, such a conformation can be easily confirmed using UV spectral analysis and NOE measurement, indicating that a detailed discussion of the conformation of the derivative is unnecessary. Furthermore, we also established another method for the determination of the absolute configurations of an acyclic secondary alcohol using FFDNB in combination with usual reversed phase HPLC as the recognition. This methodology is based on the formation of the fixed favorable conformation of a secondary alcohol-DLA (-2,4-dinitrophenyl-5-leucinamide) derivative and its recognition by ODS silica gel. Basically, this method can be applied to acyclic secondary alcohols in the same manner as the case of primary amines. Through these studies we have developed a total system for the determination of the absolute configuration of secondary alcohols and primary amines, in which a fixed conformation is formed using the characteristic functions of FFDNB and the resulting conformation is recognized by NMR spectroscopy or HPLC.
天然有機化合物討論会の論文
1999-09-01

73(P55) ジフルオロジニトロベンゼンを用いた二級アルコール絶対配置決定法(ポスター発表の部)

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