29 CD差スペクトル法による鎖状ポリオールの絶対配置の決定(口頭発表の部)
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概要
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A general method based on difference circular dichroic spectroscopy for assigning multiple chiral centers in acyclic polyols is presented. The validity of this method was demonstrated using twelve 1,2,4-triols, eight 1,2,4,6-tetrols, and four 1,2,4,6,8,10-hexols as model componds with established absolute configuration. Model Polyols were transformed into two acylated derivatives; perbenzoates (II) and 1-0-pivaloyl-perbenzoates (III). Subtraction of the CD spectrum of III from that of II gave a difference CD (DIF CD) spectrum, where benzoate/benzoate interactions between the secondary chiral centers canceled out. The Cotton effect of the DIF CD spectrum reflects only the exciton interaction of the terminal 1,2-dibenzoate system. A positive sign of the DIF CD is correlated with (2S)-configuration and a negative one with (2S)-configuration. The intensity of the Cotton effect (A-Value) is diagnostic of the relative configuration of 2,4-positions. In the case of 2,4-syn isomers, the absolute value of A is higher than 10, whereas that of 2,4-anti isomers shows below 10. Moreover, in the CD study of 1-0-pivaloyl-2,4,6-tri-benzoates the following general rule is concluded: either a distinctive negative or positive couplet is observed if the tribenzoate contains odd number of 1,3-anti moieties or a very weak couplet if an even number of 1,3-anti or 1,3-syn moieties are present. Combination of this rule and the DIF CD method allowed us to determine the absolue configuration of 1,2,4,6-tetrols, even if the relative stereochemistry is unkown.
- 天然有機化合物討論会の論文
- 1993-09-10
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