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Activation of allylic esters in an intramolecular vinylogous kinetic resolution reaction with synergistic magnesium catalysts

Author

Listed:
  • Dan Li

    (Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University)

  • Yuling Yang

    (Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University)

  • Minmin Zhang

    (Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University)

  • Linqing Wang

    (Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University)

  • Yingfan Xu

    (Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University)

  • Dongxu Yang

    (Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University)

  • Rui Wang

    (Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University)

Abstract

Kinetic resolution (KR) of racemic starting materials is a powerful and practical alternative to prepare valuable enantiomerically enriched compounds. A magnesium-catalyzed kinetic resolution based on a designed intramolecular vinylogous Michael reaction is disclosed. Here we show a synergistic catalytic strategy based on the development of chiral ligands. Substrates containing linear allylic ester structures are designed and synthesized to construct key [6.6.5]-tricyclic chiral skeletons via this kinetic resolution process. Detailed mechanistic studies reveal a rational mechanism for the current intramolecular vinylogous KR reaction. The desired direct intramolecular asymmetric vinylogous Michael reaction of linear allylic esters is realized in high efficiency and enantioselectivity with the synergistic catalytic system.

Suggested Citation

  • Dan Li & Yuling Yang & Minmin Zhang & Linqing Wang & Yingfan Xu & Dongxu Yang & Rui Wang, 2020. "Activation of allylic esters in an intramolecular vinylogous kinetic resolution reaction with synergistic magnesium catalysts," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-16486-0
    DOI: 10.1038/s41467-020-16486-0
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