Aza-Oxyallyl Cation Driven 3‑Amido Oxetane Rearrangement to 2‑Oxazolines: Access to Oxazoline Amide Ethers

Herein, we report a highly facile and unprecedented activation of 3-amido oxetanes to synthesize 2-oxazoline amide ethers using a transient electrophilic aza-oxyallyl cation as an activating as well as an alkylating agent under mild reaction conditions. The aza-oxyallyl cation driven intramolecular...

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Veröffentlicht in:Journal of organic chemistry 2022-03, Vol.87 (5), p.2155-2166
Hauptverfasser: Taily, Irshad Maajid, Saha, Debarshi, Banerjee, Prabal
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Sprache:eng
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Zusammenfassung:Herein, we report a highly facile and unprecedented activation of 3-amido oxetanes to synthesize 2-oxazoline amide ethers using a transient electrophilic aza-oxyallyl cation as an activating as well as an alkylating agent under mild reaction conditions. The aza-oxyallyl cation driven intramolecular rearrangement of 3-amido oxetanes to 2-oxazolines is the hallmark of this transformation and is a new addition to the reactivity profile of aza-oxyallyl cations.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c03108