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

Sean P. Bew; Simon J. Coles; Mateusz B. Pitak; Wim T. Klooster; Polly-Anna Ashford; Victor Zdorichenko

doi:10.1016/j.tet.2019.130532

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

Sean P. Bew (Lead Author)
, Simon J. Coles
, Mateusz B. Pitak
, Wim T. Klooster
, Polly-Anna Ashford
, Victor Zdorichenko

Synthetic and Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

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.

Original language	English
Article number	130532
Journal	Tetrahedron
Volume	75
Issue number	42
Early online date	19 Aug 2019
DOIs	https://doi.org/10.1016/j.tet.2019.130532
Publication status	Published - 18 Oct 2019

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10.1016/j.tet.2019.130532

https://www.sciencedirect.com/science/article/pii/S0040402019308658?via%3Dihub

Cite this

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title = "Generating cis-aza-diaryl and triaryl ethers via organoBr{\o}nsted acid catalysed aza-Darzens chemistry",

abstract = "We report the efficient combination of SNAr and organic Br{\o}nsted 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.",

author = "Bew, \{Sean P.\} and Coles, \{Simon J.\} and Pitak, \{Mateusz B.\} and Klooster, \{Wim T.\} and Polly-Anna Ashford and Victor Zdorichenko",

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doi = "10.1016/j.tet.2019.130532",

language = "English",

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journal = "Tetrahedron",

issn = "0040-4020",

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T1 - Generating cis-aza-diaryl and triaryl ethers via organoBrønsted acid catalysed aza-Darzens chemistry

AU - Bew, Sean P.

AU - Coles, Simon J.

AU - Pitak, Mateusz B.

AU - Klooster, Wim T.

AU - Ashford, Polly-Anna

AU - Zdorichenko, Victor

PY - 2019/10/18

Y1 - 2019/10/18

N2 - 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.

AB - 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.

U2 - 10.1016/j.tet.2019.130532

DO - 10.1016/j.tet.2019.130532

M3 - Article

SN - 0040-4020

VL - 75

JO - Tetrahedron

JF - Tetrahedron

IS - 42

M1 - 130532

ER -