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Enantioselective Ugi and Ugi-azide reactions catalyzed by anionic stereogenic-at-cobalt(III) complexes

Author

Listed:
  • Bing-Bing Sun

    (Anhui Agricultural University)

  • Kun Liu

    (Anhui Agricultural University)

  • Quan Gao

    (Anhui Agricultural University)

  • Wei Fang

    (Anhui Agricultural University)

  • Shuang Lu

    (Anhui Agricultural University)

  • Chun-Ru Wang

    (Anhui Agricultural University)

  • Chuan-Zhi Yao

    (Anhui Agricultural University)

  • Hai-Qun Cao

    (Anhui Agricultural University)

  • Jie Yu

    (Anhui Agricultural University
    Anhui Agricultural University)

Abstract

Ugi reactions and related variations are proven to be atom and step-economic strategies for construction of highly valuable peptide-like skeletons and nitrogenous heterocycles. The development of structurally diverse range of novel catalytic systems and the discovery of new approaches to accommodate a broader scope of terminating reagents for asymmetric Ugi four-component reaction is still in high demand. Here, we report a strategy that enables enantioselective Ugi four-component and Ugi-azide reactions employing anionic stereogenic-at-cobalt(III) complexes as catalysts. The key nitrilium intermediates, generated through the nucleophilic addition of isocyanides to the chiral ion-pair which consists of stereogenic-at-cobalt(III) complexes counteranion and a protonated iminium, are trapped by either carboxylic acids or in situ-generated hydrazoic acid, delivering α-acylamino amides and α-aminotetrazoles in good to excellent enantioselectivities (up to 99:1 e.r.).

Suggested Citation

  • Bing-Bing Sun & Kun Liu & Quan Gao & Wei Fang & Shuang Lu & Chun-Ru Wang & Chuan-Zhi Yao & Hai-Qun Cao & Jie Yu, 2022. "Enantioselective Ugi and Ugi-azide reactions catalyzed by anionic stereogenic-at-cobalt(III) complexes," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-34887-1
    DOI: 10.1038/s41467-022-34887-1
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