4.8 Article

Desymmetrizing Isomerization of Alkene via Thiazolinyl Iminoquinoline Cobalt Catalysis

Journal

ORGANIC LETTERS
Volume 24, Issue 5, Pages 1158-1163

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c04237

Keywords

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Funding

  1. National Key R&D Program of China [2021YFA1500200, 2021YFF0701600]
  2. Zhejiang Provincial Natural Science Foundation of China [LR19B020001]
  3. NSFC [21922107]
  4. Center of Chemistry for Frontier Technologies

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A cobalt-catalyzed desymmetrizing isomerization of exocyclic alkenes to generate chiral 1-methylcyclohexene derivatives with good yields and enantioselectivities was reported. A novel chiral thiazolinyl iminoquinoline ligand and its cobalt complex were designed and synthesized to control the establishment of tertiary or quaternary carbon centers at a remote position. This protocol is operationally simple, and a model for the stereochemical outcome has been proposed.
We report a cobalt-catalyzed desymmetrizing isomerization of exocyclic alkenes to generate chiral 1-methylcyclohexene derivatives with good yields and enantioselectivities. A novel chiral thiazolinyl iminoquinoline ligand and its cobalt complex were designed and synthesized to control the establishment of tertiary or quaternary carbon centers at a remote position. This protocol is operationally simple, and a model for the stereochemical outcome has been proposed.

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