4.6 Article

Organocatalytic asymmetric synthesis of quaternary α-isoxazole-α-alkynyl amino acid derivatives

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 45, Pages 8849-8854

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob01746f

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Funding

  1. National Natural Science Foundation of China [21672208]
  2. Startup Fund for Recruited Talent of Xihua University [Z201098]

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An enantioselective addition reaction catalyzed by a chiral phosphoric acid has been developed for the synthesis of quaternary alpha-isoxazole-alpha-alkynyl amino acid derivatives. The reaction showed high yields and good to excellent enantioselectivities, and the hydrogen-bonding interaction between the amino-isoxazole and chiral phosphoric acid played a vital role in the selectivity.
An enantioselective addition of 5-amino-isoxazoles with beta,gamma-alkynyl-alpha-ketimino esters catalyzed by a chiral phosphoric acid has been developed. This procedure allowed the formation of quaternary alpha-isoxazole-alpha-alkynyl amino acid derivatives with high yields (up to 99%) and good to excellent enantioselectivities (up to 97%), and the corresponding products enabled many further elaborations. The control experiment revealed that the hydrogen-bonding interaction of 5-amino-isoxazole with the chiral phosphoric acid played a vital role in the enantioselectivity, and the transition state of the reaction was proposed.

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