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Organocatalytic atroposelective construction of axially chiral N, N- and N, S-1,2-azoles through novel ring formation approach

Author

Listed:
  • Yu Chang

    (Chongqing University)

  • Chuandong Xie

    (Chongqing University)

  • Hong Liu

    (Chongqing University)

  • Shengli Huang

    (Chongqing University)

  • Pengfei Wang

    (Chongqing University)

  • Wenling Qin

    (Chongqing University)

  • Hailong Yan

    (Chongqing University)

Abstract

1,2-Azoles are privileged structures in ligand/catalyst design and widely exist in many important natural products and drugs. In this report, two types of axially chiral 1,2-azoles (naphthyl-isothiazole S-oxides with a stereogenic sulfur center and atropoisomeric naphthyl pyrazoles) are synthesized via modified vinylidene ortho-quinone methide intermediates. Diverse products are acquired in satisfying yields and good to excellent enantioselectivities. The vinylidene ortho-quinone methide intermediates bearing two hetero atoms at 5-position have been demonstrated as a platform molecule for the atroposelective synthesis of axially chiral 1,2-azoles. This finding not only enrich our knowledge of vinylidene ortho-quinone methide chemistry but also provide the easy preparation method for diverse atropisomeric heterobiaryls that were inaccessible by existing methodologies. The obtained chiral naphthyl-isothiazole S-oxides and naphthyl-pyrazoles have demonstrated their potential application in further synthetic transformations and therapeutic agents.

Suggested Citation

  • Yu Chang & Chuandong Xie & Hong Liu & Shengli Huang & Pengfei Wang & Wenling Qin & Hailong Yan, 2022. "Organocatalytic atroposelective construction of axially chiral N, N- and N, S-1,2-azoles through novel ring formation approach," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-29557-1
    DOI: 10.1038/s41467-022-29557-1
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    1. Mariya M. Kucherenko & Halyna R. Shcherbata, 2018. "Stress-dependent miR-980 regulation of Rbfox1/A2bp1 promotes ribonucleoprotein granule formation and cell survival," Nature Communications, Nature, vol. 9(1), pages 1-20, December.
    2. Ferdinand H. Lutter & Lucie Grokenberger & Luca Alessandro Perego & Diego Broggini & Sébastien Lemaire & Simon Wagschal & Paul Knochel, 2020. "Regioselective functionalization of aryl azoles as powerful tool for the synthesis of pharmaceutically relevant targets," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    3. Kento Ojima & Kazuki Shiraiwa & Kyohei Soga & Tomohiro Doura & Mikiko Takato & Kazuhiro Komatsu & Michisuke Yuzaki & Itaru Hamachi & Shigeki Kiyonaka, 2021. "Ligand-directed two-step labeling to quantify neuronal glutamate receptor trafficking," Nature Communications, Nature, vol. 12(1), pages 1-14, December.
    4. Thomas F. Durand-Reville & Alita A. Miller & John P. O’Donnell & Xiaoyun Wu & Mark A. Sylvester & Satenig Guler & Ramkumar Iyer & Adam B. Shapiro & Nicole M. Carter & Camilo Velez-Vega & Samir H. Mous, 2021. "Rational design of a new antibiotic class for drug-resistant infections," Nature, Nature, vol. 597(7878), pages 698-702, September.
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