4.8 Article

Three-Component Synthesis of α-Aminoperoxides Using Primary and Secondary Dialkylzinc Reagents with O2 and α-Amido Sulfones

Journal

ORGANIC LETTERS
Volume 22, Issue 14, Pages 5380-5384

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01692

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Funding

  1. Agencia Estatal de Investigacion (AEI, Spanish Government)
  2. Fondo Europeo de Desarrollo Regional (FEDER, European Union) [CTQ2017-84900-P]
  3. MINECO (Gobierno de Espana) [CTQ2013-47494-P]
  4. Generalitat Valenciana
  5. European Social Fund
  6. Spanish Government [IJC2018-036682-I]

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A straightforward strategy for the synthesis of unprecedented alpha-aminoperoxides bearing primary and secondary alkylperoxide substituents is described. Commercially available dialkylzinc reagents are oxidized with molecular oxygen and the consequent peroxide species react with stable (hetero)aromatic and aliphatic alpha-amido sulfones in excellent yields (>90%). The now available alpha-aminoperoxides are of potential interest in medicinal chemistry, specifically for the synthesis of antimalarial compounds. Moreover, modification of the reaction conditions selectively leads to N,O-acetals in good yields.

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