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

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...

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Detalles Bibliográficos
Autores principales: Bew, Sean P., Liddle, John, Hughes, David L., Pesce, Paolo, Thurston, Sean M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5502890/
https://www.ncbi.nlm.nih.gov/pubmed/28378388
http://dx.doi.org/10.1002/anie.201611990
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author Bew, Sean P.
Liddle, John
Hughes, David L.
Pesce, Paolo
Thurston, Sean M.
author_facet Bew, Sean P.
Liddle, John
Hughes, David L.
Pesce, Paolo
Thurston, Sean M.
author_sort Bew, Sean P.
collection PubMed
description 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.
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spelling pubmed-55028902017-07-24 Chiral Brønsted Acid‐Catalyzed Asymmetric Synthesis of N‐Aryl‐cis‐aziridine Carboxylate Esters Bew, Sean P. Liddle, John Hughes, David L. Pesce, Paolo Thurston, Sean M. Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2017-04-05 2017-05-02 /pmc/articles/PMC5502890/ /pubmed/28378388 http://dx.doi.org/10.1002/anie.201611990 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Bew, Sean P.
Liddle, John
Hughes, David L.
Pesce, Paolo
Thurston, Sean M.
Chiral Brønsted Acid‐Catalyzed Asymmetric Synthesis of N‐Aryl‐cis‐aziridine Carboxylate Esters
title Chiral Brønsted Acid‐Catalyzed Asymmetric Synthesis of N‐Aryl‐cis‐aziridine Carboxylate Esters
title_full Chiral Brønsted Acid‐Catalyzed Asymmetric Synthesis of N‐Aryl‐cis‐aziridine Carboxylate Esters
title_fullStr Chiral Brønsted Acid‐Catalyzed Asymmetric Synthesis of N‐Aryl‐cis‐aziridine Carboxylate Esters
title_full_unstemmed Chiral Brønsted Acid‐Catalyzed Asymmetric Synthesis of N‐Aryl‐cis‐aziridine Carboxylate Esters
title_short Chiral Brønsted Acid‐Catalyzed Asymmetric Synthesis of N‐Aryl‐cis‐aziridine Carboxylate Esters
title_sort chiral brønsted acid‐catalyzed asymmetric synthesis of n‐aryl‐cis‐aziridine carboxylate esters
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5502890/
https://www.ncbi.nlm.nih.gov/pubmed/28378388
http://dx.doi.org/10.1002/anie.201611990
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