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Development of bifunctional organocatalysts and application to asymmetric total synthesis of naucleofficine I and II

Author

Listed:
  • Yong-Hai Yuan

    (Lanzhou University)

  • Xue Han

    (Lanzhou University)

  • Fu-Ping Zhu

    (Lanzhou University)

  • Jin-Miao Tian

    (School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University)

  • Fu-Min Zhang

    (Lanzhou University)

  • Xiao-Ming Zhang

    (Lanzhou University)

  • Yong-Qiang Tu

    (Lanzhou University
    School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University)

  • Shao-Hua Wang

    (Lanzhou University)

  • Xiang Guo

    (Lanzhou University)

Abstract

The proline-type organocatalysts has been efficiently employed to catalyze a wide range of asymmetric transformations; however, there are still many synthetically useful and challenging transformations that remain unachievable in an asymmetric fashion. Herein, a chiral bifunctional organocatalyst with a spirocyclic pyrrolidine backbone-derived containing fluoro-alkyl and aryl sulfonamide functionalities, are designed, prepared, and examined in the asymmetric Mannich/acylation/Wittig reaction sequence of 3,4-dihydro-β-carboline with acetaldehyde, acyl halides, and Wittig reagents. As a result, the spirocyclic pyrrolidine trifluoromethanesulfonamide catalyst can facilitate this versatile sequence as demonstrated by 18 examples displaying excellent enantioselectivity (up to 94% ee), as well as moderate to good yields (up to 54% over 3 steps). As a practical application, the asymmetric total synthesis of naucleofficine I (1a) and II (1b) in ten steps have been accomplished.

Suggested Citation

  • Yong-Hai Yuan & Xue Han & Fu-Ping Zhu & Jin-Miao Tian & Fu-Min Zhang & Xiao-Ming Zhang & Yong-Qiang Tu & Shao-Hua Wang & Xiang Guo, 2019. "Development of bifunctional organocatalysts and application to asymmetric total synthesis of naucleofficine I and II," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-11382-8
    DOI: 10.1038/s41467-019-11382-8
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