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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タイトル別名
  • Selective Molecular Transformation of 1, 2-Diols Based on Molecular Recognition
  • 1 2 ジオール ブンシ ニンシキ ニ モトズク センタクテキ ブンシ ヘンカン ハンノウ

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On the bases of the concept that a coordination of 1, 2-diols 1 with an appropriate metal ion (Mn+) 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 Mn+. 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) -CuCl2 as a catalyst. In particular, the asymmetric outcome using (R, R) -Ph-BOX-CuCl2 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-1, 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).

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