4.8 Article

Ruthenium-Catalyzed Asymmetric N-Acyl Nitrene Transfer Reaction: Imidation of Sulfide

Journal

ORGANIC LETTERS
Volume 22, Issue 10, Pages 4021-4025

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01373

Keywords

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Funding

  1. JSPS KAKENHI [18H04264]
  2. MEXT, Japan
  3. Grants-in-Aid for Scientific Research [18H04264] Funding Source: KAKEN

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The asymmetric nitrene transfer reaction is a useful and strong tool for the construction of nitrogen functional groups such as N-sulfonyl amide and carbamic ester in a highly enantioselective manner. On the other hand, there is a substantial limitation in this filed: the transfer of N-acyl amide via the corresponding nitrene intermediates is still difficult because N-acyl nitrenes undergo undesired nitrene dimerization or Curtius rearrangement. Herein, we achieved highly enantioselective imidation of sulfides via catalytic N-acyl nitrene transfer with (OC)ruthenium-salen complex 2b as the catalyst and 3-substituted 1,4,2-dioxazol-5-ones 1 as the nitrene source. Complex 2b can decompose dioxazolones 1 to the desired N-acyl nitrene intermediates without any activation via heating or UV irradiation, or transfer generating nitrene intermediates to the sulfur atom of sulfides with good to excellent enantioselectivities (<= 98% ee) without diazene and isocyanate contamination.

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