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<p>The mechanism of spontaneous chirality generation remains not sufficiently explored, and compounds with a structure significantly different from the known Soai substrates are elusive. Recently we reported enantioselective reduction of 3-acetylpyridine with dicyclopentylzinc in the presence of a chiral catalyst. In this work, the interaction of 2- and 3-pyridyl ketones with dicyclopentylzinc in the absence and presence of a chiral catalyst was investigated. It is shown that all ketones are reduced by the organozinc reagent to the corresponding secondary alcohols. Low enantioselectivity (28% <i>ee</i>) was observed only in the reaction of a 3-acetylpyridine derivative carried out in the presence of a chiral amino alcohol. To explain the stereoselectivity of 3-acetylpyridine reduction, quantum chemical calculations were used.</p>

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Reactions of pyridine ketones with dicyclopentylzinc

  • 期刊论文

  • 发表日期：

    2025年3月1日

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  • L. Z. Latypova,
  • E. Sh. Saigitbatalova,
  • O. A. Mikhailov,
  • N. S. Charushin,
  • A. A. Zagidullin,
  • A. R. Kurbangalieva,
  • I. D. Gridnev

摘要

The mechanism of spontaneous chirality generation remains not sufficiently explored, and compounds with a structure significantly different from the known Soai substrates are elusive. Recently we reported enantioselective reduction of 3-acetylpyridine with dicyclopentylzinc in the presence of a chiral catalyst. In this work, the interaction of 2- and 3-pyridyl ketones with dicyclopentylzinc in the absence and presence of a chiral catalyst was investigated. It is shown that all ketones are reduced by the organozinc reagent to the corresponding secondary alcohols. Low enantioselectivity (28% ee) was observed only in the reaction of a 3-acetylpyridine derivative carried out in the presence of a chiral amino alcohol. To explain the stereoselectivity of 3-acetylpyridine reduction, quantum chemical calculations were used.