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

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
Related URLs:	http://onlinelibrary.wiley.com/doi/10.10...
Depositing User:	Pure Connector
Date Deposited:	13 Jun 2017 05:05
Last Modified:	22 Oct 2022 02:34
URI:	https://ueaeprints.uea.ac.uk/id/eprint/63728
DOI:	10.1002/anie.201611990

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