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Aza-Quasi-Favorskii Reaction: Construction of Highly Substituted Aziridines through a Concerted Multibond Rearrangement Process.
Kattamuri, Padmanabha V; Zhao, Jidong; Das, Tamal Kanti; Siitonen, Juha H; Morgan, Nathan; Ess, Daniel H; Kürti, László.
Affiliation
  • Kattamuri PV; Department of Chemistry, Rice University, Houston, Texas 77030, United States.
  • Zhao J; Department of Chemistry, Rice University, Houston, Texas 77030, United States.
  • Das TK; Department of Chemistry, Rice University, Houston, Texas 77030, United States.
  • Siitonen JH; Department of Chemistry, Rice University, Houston, Texas 77030, United States.
  • Morgan N; Department of Chemistry and Materials Science, Aalto University, Kemistintie 1, FI-02150 Espoo, Finland.
  • Ess DH; Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, United States.
  • Kürti L; Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, United States.
J Am Chem Soc ; 144(24): 10943-10949, 2022 06 22.
Article in En | MEDLINE | ID: mdl-35674783
ABSTRACT
A new molecular rearrangement, the aza-Quasi-Favorskii rearrangement, has been developed for the construction of highly substituted aziridines. Electron-deficient O-sulfonyl oximes react readily with α,α-disubstituted acetophenone-derived enolates to furnish highly substituted aziridines via this unprecedented domino process. In-depth computational studies reveal an asynchronous yet concerted nitrenoid-type rearrangement pathway.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Aziridines Language: En Journal: J Am Chem Soc Year: 2022 Document type: Article Affiliation country: United States
Fulltext
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Aziridines Language: En Journal: J Am Chem Soc Year: 2022 Document type: Article Affiliation country: United States