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Generating cis-aza-diaryl and triaryl ethers via organoBrønsted acid catalysed aza-Darzens chemistry

Generating cis-aza-diaryl and triaryl ethers via organoBrønsted acid catalysed aza-Darzens chemistry
Generating cis-aza-diaryl and triaryl ethers via organoBrønsted acid catalysed aza-Darzens chemistry

We report the efficient combination of SNAr and organic Brønsted acid catalysis protocols for the construction of cis-aziridine-derived biaryl and triaryl ethers. Using aza-Darzens chemistry mono-cis-aziridine-biaryl and bis-(cis-aziridine)-triaryl ethers have been generated; these motifs have significant potential as easily synthesised, functionalised precursors of a glycopeptide backbone.

Aza-Darzens, Aziridine, Catalysis, Glycopeptide, Organic Brønsted acid, SAr
0040-4020
1-12
Bew, Sean P.
29f9b4b4-41cc-4bd2-b75c-01ae8349bf3e
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Pitak, Mateusz B.
eeb6a00f-2291-4376-830f-d30dfd607ed1
Klooster, W. T.
64dc0111-f415-4226-9189-45764c0933d9
Ashford, Polly Anna
7dab6213-f267-4ae4-a683-3231b425cc57
Zdorichenko, Victor
ab3c4558-d380-4962-af0f-5e23a3ef33c6
Bew, Sean P.
29f9b4b4-41cc-4bd2-b75c-01ae8349bf3e
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Pitak, Mateusz B.
eeb6a00f-2291-4376-830f-d30dfd607ed1
Klooster, W. T.
64dc0111-f415-4226-9189-45764c0933d9
Ashford, Polly Anna
7dab6213-f267-4ae4-a683-3231b425cc57
Zdorichenko, Victor
ab3c4558-d380-4962-af0f-5e23a3ef33c6

Bew, Sean P., Coles, Simon J., Pitak, Mateusz B., Klooster, W. T., Ashford, Polly Anna and Zdorichenko, Victor (2019) Generating cis-aza-diaryl and triaryl ethers via organoBrønsted acid catalysed aza-Darzens chemistry. Tetrahedron, 75 (42), 1-12, [130532]. (doi:10.1016/j.tet.2019.130532).

Record type: Article

Abstract

We report the efficient combination of SNAr and organic Brønsted acid catalysis protocols for the construction of cis-aziridine-derived biaryl and triaryl ethers. Using aza-Darzens chemistry mono-cis-aziridine-biaryl and bis-(cis-aziridine)-triaryl ethers have been generated; these motifs have significant potential as easily synthesised, functionalised precursors of a glycopeptide backbone.

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More information

Accepted/In Press date: 14 August 2019
e-pub ahead of print date: 19 August 2019
Published date: 18 October 2019
Keywords: Aza-Darzens, Aziridine, Catalysis, Glycopeptide, Organic Brønsted acid, SAr

Identifiers

Local EPrints ID: 436156
URI: http://eprints.soton.ac.uk/id/eprint/436156
ISSN: 0040-4020
PURE UUID: 1e7fdcbb-d634-47f7-b51a-acc1572f305b
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Mateusz B. Pitak: ORCID iD orcid.org/0000-0002-3680-7100

Catalogue record

Date deposited: 29 Nov 2019 17:30
Last modified: 18 Feb 2021 16:53

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Contributors

Author: Sean P. Bew
Author: Simon J. Coles ORCID iD
Author: Mateusz B. Pitak ORCID iD
Author: W. T. Klooster
Author: Polly Anna Ashford
Author: Victor Zdorichenko

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