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

Bew, Sean P., Liddle, John, Hughes, David L., Pesce, Paolo and Thurston, Sean M. (2017) Chiral Brønsted Acid-Catalyzed Asymmetric Synthesis of N-Aryl-cis-aziridine Carboxylate Esters. Angewandte Chemie International Edition, 56 (19). 5322–5326. ISSN 1433-7851

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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.

Item Type: Article
Uncontrolled Keywords: asymmetrische katalyse,aziridine,brønsted-säuren,mehrkomponentenreaktionen
Faculty \ School: Faculty of Science > School of Chemistry
Related URLs:
Depositing User: Pure Connector
Date Deposited: 13 Jun 2017 05:05
Last Modified: 25 Jun 2020 00:10
URI: https://ueaeprints.uea.ac.uk/id/eprint/63728
DOI: 10.1002/anie.201611990

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