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- Title
Chiral Brønsted Acid-Catalyzed Asymmetric Synthesis of N-Aryl- cis-aziridine Carboxylate Esters.
- Authors
Bew, Sean P.; Liddle, John; Hughes, David L.; Pesce, Paolo; Thurston, Sean M.
- 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.
- Subjects
BRONSTED acids; DARZENS reaction; CHEMICAL reactions; ALDEHYDES; CHLORAMPHENICOL; ANTIBACTERIAL agents
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 19, p5406
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201611990