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

Authors :
Taily IM
Saha D
Banerjee P
Source :
The Journal of organic chemistry [J Org Chem] 2022 Mar 04; Vol. 87 (5), pp. 2155-2166. Date of Electronic Publication: 2022 Feb 07.
Publication Year :
2022

Abstract

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.

Details

Language :
English
ISSN :
1520-6904
Volume :
87
Issue :
5
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
35129349
Full Text :
https://doi.org/10.1021/acs.joc.1c03108