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Iron-catalyzed stereoselective C–H alkylation for simultaneous construction of C–N axial and C-central chirality

Author

Listed:
  • Zi-Jing Zhang

    (Georg-August-Universität Göttingen)

  • Nicolas Jacob

    (ECPM)

  • Shilpa Bhatia

    (University of Rochester)

  • Philipp Boos

    (Georg-August-Universität Göttingen)

  • Xinran Chen

    (Georg-August-Universität Göttingen
    Zhejiang University)

  • Joshua C. DeMuth

    (University of Rochester)

  • Antonis M. Messinis

    (Georg-August-Universität Göttingen)

  • Becky Bongsuiru Jei

    (Georg-August-Universität Göttingen)

  • João C. A. Oliveira

    (Georg-August-Universität Göttingen)

  • Aleksa Radović

    (University of Rochester)

  • Michael L. Neidig

    (University of Oxford)

  • Joanna Wencel-Delord

    (ECPM
    Universität Würzburg)

  • Lutz Ackermann

    (Georg-August-Universität Göttingen
    Georg-August-Universität Göttingen)

Abstract

The assembly of chiral molecules with multiple stereogenic elements is challenging, and, despite of indisputable advances, largely limited to toxic, cost-intensive and precious metal catalysts. In sharp contrast, we herein disclose a versatile C–H alkylation using a non-toxic, low-cost iron catalyst for the synthesis of substituted indoles with two chiral elements. The key for achieving excellent diastereo- and enantioselectivity was substitution on a chiral N-heterocyclic carbene ligand providing steric hindrance and extra represented by noncovalent interaction for the concomitant generation of C–N axial chirality and C-stereogenic center. Experimental and computational mechanistic studies have unraveled the origin of the catalytic efficacy and stereoselectivity.

Suggested Citation

  • Zi-Jing Zhang & Nicolas Jacob & Shilpa Bhatia & Philipp Boos & Xinran Chen & Joshua C. DeMuth & Antonis M. Messinis & Becky Bongsuiru Jei & João C. A. Oliveira & Aleksa Radović & Michael L. Neidig & , 2024. "Iron-catalyzed stereoselective C–H alkylation for simultaneous construction of C–N axial and C-central chirality," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-47589-7
    DOI: 10.1038/s41467-024-47589-7
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    References listed on IDEAS

    as
    1. Zi-Jing Zhang & Shu-Wen Li & João C. A. Oliveira & Yanjun Li & Xinran Chen & Shuo-Qing Zhang & Li-Cheng Xu & Torben Rogge & Xin Hong & Lutz Ackermann, 2023. "Data-driven design of new chiral carboxylic acid for construction of indoles with C-central and C–N axial chirality via cobalt catalysis," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    2. Matthew N. Hopkinson & Christian Richter & Michael Schedler & Frank Glorius, 2014. "An overview of N-heterocyclic carbenes," Nature, Nature, vol. 510(7506), pages 485-496, June.
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