YoungKu Kang, Matthew T. Richers, Conrad H. Sawicki and Daniel Seidel
Chem. Commun., 2015,51, 10648-10651
DOI:
10.1039/C5CC03390J,
Communication
Cyclic amines such as pyrrolidine and 1,2,3,4-tetrahydroisoquinoline undergo redox-annulations with α,β-unsaturated aldehydes and ketones. Carboxylic acid promoted generation of a conjugated azomethine ylide is followed by 6π-electrocylization, and, in some cases, tautomerization. The resulting ring-fused pyrrolines are readily oxidized to the corresponding pyrroles or reduced to pyrrolidines.
