Reusable Selenenyl Iodide-Initiated Cascade Cyclization of Polyenes with N-terminating Groups.

ABSTRACT: Although cascade cyclization of polyenes has advanced remarkably, most reported examples are limited to carbon- or oxygen-terminating groups, with nitrogen-terminating cyclizations remaining rare. In this work, we developed a cascade cyclization of polyenes with N-terminating groups, initiated by an isolable selenenyl iodide (RSeI) bearing a cavity-shaped substituent. Acid-labile substrates were successfully employed in the cascade cyclization. Compared with commonly used organoselenium reagents, a selenenyl iodide, characterized by its unique soft electrophilic nature, proved to be the most effective in promoting the cascade reaction. Furthermore, the stabilizing effect of the cavity-shaped substituent enabled the isolation of a selenenic acid (RSeOH), which was generated via oxidative β-

SUBMITTER: Kuwano S 

PROVIDER: S-EPMC12282649 | biostudies-literature | 2025 Jul

REPOSITORIES: biostudies-literature