Regio- and stereoselective synthesis of thiazoline derivatives via the thioketene-induced ring expansion of aziridines?

Chemical Communications Pub Date: 2022-01-27 DOI: 10.1039/D1CC06535A

Abstract

Metal-free thioketene-induced ring expansion of aziridines gave 4-alkylthiazolines stereospecifically from 2-alkylaziridines through an intramolecular substitution at the less substituted ring carbon and 5-arylthiazolines stereoselectively from 2-arylaziridines via tandem ring cleavage and formation through intimate ion-pair intermediates after nucleophilic addition of aziridines to thioketenes generated from 4-substituted 1,2,3-thiadiazoles in the presence of a base.

Graphical abstract: Regio- and stereoselective synthesis of thiazoline derivatives via the thioketene-induced ring expansion of aziridines
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