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Molecules (Basel, Switzerland)
Dec 17, 2022;27 (24):

Atroposelective Amination of Indoles via Chiral Center Induced Chiral Axis Formation.

Yong Wang, Jingxue Yan, Yiqing Jiang, Zexuan Wei, Zhenlin Tu, Chao Dong, Tao Lu, Yadong Chen, Jie Feng
Author Information
  1. Yong Wang: Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, Nanjing 210009, China.
  2. Jingxue Yan: Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, Nanjing 210009, China.
  3. Yiqing Jiang: Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, Nanjing 210009, China.
  4. Zexuan Wei: Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, Nanjing 210009, China.
  5. Zhenlin Tu: Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, Nanjing 210009, China.
  6. Chao Dong: Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, Nanjing 210009, China.
  7. Tao Lu: Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, Nanjing 210009, China.
  8. Yadong Chen: Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, Nanjing 210009, China.
  9. Jie Feng: Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, Nanjing 210009, China.
PMID: 36558141 DOI: 10.3390/molecules27249008

Abstract

The construction of an N-C chiral axis for N-aryl indole derivatives is meaningful as they widely exist in functionalized molecules. This work provides a novel method for this purpose via amination of amino acid derivatives at the C2 position of the indole and chiral center induced chiral axis formation. The protocol of this transformation is easily accessible, not requiring metal or an organic chiral catalyst, endowing this method with great potential in the construction of axis chiral -aryl indoles.

Keywords

amination amino acid atropisomers central-to-axial indole skeleton

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Grants

  1. 81973182/National Natural Science Foundation of China
  2. 81673301/National Natural Science Foundation of China

MeSH Term

Amination
Indoles
Catalysis

Chemicals

Indoles
Journal Article

Word Cloud

Created with Highcharts 10.0.0chiralaxisindoleconstructionderivativesmethodviaaminationaminoacidChiralN-CN-arylmeaningfulwidelyexistfunctionalizedmoleculesworkprovidesnovelpurposeC2positioncenterinducedformationprotocoltransformationeasilyaccessiblerequiringmetalorganiccatalystendowinggreatpotential-arylindolesAtroposelectiveAminationIndolesCenterInducedAxisFormationatropisomerscentral-to-axialskeleton

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