4.8 Article

Co-Catalyzed Direct Regio- and Enantioselective Intermolecular γ-Amination of N-Acylpyrazoles

Journal

ORGANIC LETTERS
Volume 23, Issue 1, Pages 25-30

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03522

Keywords

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Funding

  1. NSFC [21672145, 51733007, 21906049]
  2. Science and Technology Commission of Shanghai Municipality [17JC1403700, 19JC1430100, 19JC1410301]
  3. Drug Innovation Major Project of the Ministry of Science and Technology of China [2018ZX09711001-005-002]

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The cobalt-catalyzed regio- and enantioselective gamma-amination of beta,gamma-unsaturated N-acylpyrazoles has been achieved, delivering the corresponding products with good regio- and enantioselectivity. DFT calculations were used to explain the selectivity of this gamma-amination, and the chiral products were easily converted into chiral gamma-amino acid derivatives.
A cobalt-catalyzed regio- and enantioselective gamma-amination of beta,gamma-unsaturated N-acylpyrazoles that delivers the corresponding gamma-amination products in good regio- and enantioselectivity has been established. Moreover, the nitrogen-containing compounds could be easily synthesized. DFT calculations have been provided to explain regio- and enantioselectivity for this gamma-amination. The chiral gamma-amination products were readily converted into the chiral gamma-amino acid derivatives.

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