Synthesis of 2,3-Disubstituted Pyrroles By Lewis Acid Promoted Cyclization of N-Sulfonyl Vinylogous Carbamates and Amides
Chemistry and Biochemistry
Mathematics and Natural Sciences
A three-step sequence to construct pyrroles from three components including 2,2-dimethoxyethylamine, aryl/alkyl sulfonyl chlorides and alkynes bearing electron-withdrawing groups is presented. The pyrroles are proposed to arise via a 5-exo-trig cyclization proceeding through both oxocarbenium and N-sulfonyliminium ions. This modular route allows for the variability at the N-sulfonyl group, the C2 and C3 substituents for rational vectoring of the pyrrole nucleus for downstream processes.
Rustin, G. J.,
Donahue, M. G.
(2023). Synthesis of 2,3-Disubstituted Pyrroles By Lewis Acid Promoted Cyclization of N-Sulfonyl Vinylogous Carbamates and Amides. Tetrahedron Letters.
Available at: https://aquila.usm.edu/fac_pubs/20995