Development of Multi-functional NHC Catalysts bearing Pyridine Moiety: Application to Catalytic Asymmetric Reactions

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  • Soeta Takahiro
    Division of Material Chemistry, Graduate School of Natural Science and Technology
  • Ukaji Yutaka
    Division of Material Chemistry, Graduate School of Natural Science and Technology

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  • 多点認識型含窒素複素環カルベンの開発と触媒的不斉反応への展開
  • タテン ニンシキガタ ガン チッソフクソカン カルベン ノ カイハツ ト ショクバイテキ フセイ ハンノウ エ ノ テンカイ

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<p>Since discovering the first stable nucleophilic carbene, the application of N-heterocyclic carbenes (NHCs) has dramatically drawn attention in organic chemistry. Recently, NHCs have become popular ligands in organometallic chemistry and many complexes incorporating NHCs have been used in organic synthesis. NHCs act as not only ligands for metal, but also as organocatalysts. The nucleophilic carbene attacks onto carbonyl groups to afford the key intermediate, so called the Breslow intermediate, which attacks to the other carbonyl compounds to afford the products. In addition, catalytic asymmetric reactions using chiral NHCs have been reported with good to excellent stereoselectivities. Here, amino acid-derived chiral triazolium and imidazolium salts, each bearing a pyridine ring, were developed as N-heterocyclic carbene organocatalysts and chiral ligands toward catalytic asymmetric reactions.</p>

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