Synthesis of 2,3-Disubstituted Pyrroles By Lewis Acid Promoted Cyclization of N-Sulfonyl Vinylogous Carbamates and Amides
Document Type
Article
Publication Date
4-19-2023
Department
Chemistry and Biochemistry
School
Mathematics and Natural Sciences
Abstract
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.
Publication Title
Tetrahedron Letters
Recommended Citation
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