Development of Innovative Hydrogen-Bond-Donor Catalysts Based on Heterocyclic Scaffolds and Their Applications to Asymmetric Reactions

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  • 複素環骨格を基盤とする新規水素結合供与型有機分子触媒の開発と不斉反応への応用
  • フクソカン コッカク オ キバン ト スル シンキ スイソ ケツゴウ キョウヨガタ ユウキ ブンシ ショクバイ ノ カイハツ ト フセイ ハンノウ エ ノ オウヨウ

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We have designed and synthesized novel bifunctional hydrogen-bond (HB) donor catalysts bearing a benzothiadiazine or a quinazoline scaffold, whose HB-donating activity as well as recognition modes of the substrates were found to be significantly different from thiourea-typed organocatalysts by comparison of their 1H NMR studies, X-ray crystallographic analyses, spectrophotometric analyses, and computational investigations. We found that quinazoline-typed catalysts were effective for the highly enantioselective hydrazination of 1,3-dicarbonyl compounds and that benzothiadiazine-type catalysts showed great activity for the asymmetric isomerization of alkynoates to allenoates. In both cases, these newly developed catalysts were much more efficient than thiourea-typed organocatalysts, indicating that the HB-donating moiety of the catalysts was important for the recognition and activation of the substrates to facilitate the reaction.

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