Chiral Brønsted Acid-Catalyzed Asymmetric Synthesis of N-Aryl-cis-aziridine Carboxylate Esters

Sean P. Bew, John Liddle, David L. Hughes, Paolo Pesce, Sean M. Thurston

Research output: Contribution to journalArticle

17 Citations (Scopus)
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Abstract

We report a multi-component asymmetric Brønsted acid-catalyzed aza-Darzens reaction which is not limited to specific aromatic or heterocyclic aldehydes. Incorporating alkyl diazoacetates and, important for high ee's, ortho-tert-butoxyaniline our optimized reaction (i.e. solvent, temperature and catalyst study) affords excellent yields (61–98 %) and mostly >90 % optically active cis-aziridines. (+)-Chloramphenicol was generated in 4 steps from commercial starting materials. A tentative mechanism is outlined.
Original languageEnglish
Pages (from-to)5322–5326
Number of pages5
JournalAngewandte Chemie International Edition
Volume56
Issue number19
Early online date5 Apr 2017
DOIs
Publication statusPublished - 2 May 2017

Keywords

  • Asymmetrische Katalyse
  • Aziridine
  • Brønsted-Säuren
  • Mehrkomponentenreaktionen

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