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Bew, Sean P. 
ORCID: https://orcid.org/0000-0002-9087-9463, 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 (former - to 2024) |
| UEA Research Groups: | Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis |
| Related URLs: | |
| Depositing User: | Pure Connector |
| Date Deposited: | 13 Jun 2017 05:05 |
| Last Modified: | 21 Oct 2024 23:45 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/63728 |
| DOI: | 10.1002/anie.201611990 |
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