1,2-ジオール分子認識に基づく選択的分子変換反応
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概要
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On the bases of the concept that a coordination of 1,2-diols 1 with an appropriate metal ion(M^n+) might form an activated five-membered intermediate in which the OH group is much activated than those of non-activated 1, we examined a monobenzoylation of 1 by benzoyl chloride using tin and copper ions as M^n+. As the results, the monobenzoylation of 1 was achieved with high selectivity even in the presence of monools. The monobenzoylation reactions were then applied to kinetic resolution of dl-1 and asymmetric desymmetrization of meso-1 using a chiral organotin or BOX(bisoxazoline)-CuCl_2 as a catalyst. In particular, the asymmetric outcome using (R, R)-Ph-BOX-CuCl_2 catalyst was promising and attractive. That is, the kinetic resolution of dl-1(with up to >99.9% ee for monobenzoylation of hydrobenzoin), its application to a synthesis of D-inositol-1-phosphate (100% ee), the asymmetric desymmetrization of meso-1(with up to 94% ee for monobenzoylation of meso-1,2-hydrobenzoin and 93% ee for monocarbamoylation of meso-l,2-cyclooctanediol), and the asymmetric desymmetrization of meso-1,3-diols(with up to 55% ee for the monobenzoylation of ethyl 2-ethyl-2-hydroxymethyl-3-hydroxypropanoate) were achieved. Also, the method was applied to electrochemical oxidation of 1 and its asymmetric version(38% ee for the asymmetric desymmetrization of meso-hydrobenzoin and 72% ee for the kinetic resolution of dl-hydrobenzoin).
- 有機合成化学協会の論文
- 2007-03-01
著者
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尾野村 治
長崎大学 大学院医歯薬学総合研究科生命薬科学専攻
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松村 功啓
長崎大学大学院医歯薬学総合研究科
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尾野村 治
長崎大 大学院医歯薬学総合研究科 生命薬科学専攻
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尾野村 治
長崎大学大学院医歯薬学総合研究科
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出水 庸介
長崎大学大学院医歯薬学総合研究科
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Demizu Yosuke
Graduate School Of Pharmaceutical Sciences Kyushu University
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Demizu Yosuke
Faculty Of Pharmaceutical Sciences At Kagawa Campus Tokushima Bunri University
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Demizu Yosuke
Division Of Organic Chemistry National Institute Of Health Sciences
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Demizu Yosuke
Division Of Organic Chemistry National Institute Of Health Sciences Ministry Of Health And Welfare
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