Catalytic, transannular carbonyl-olefin metathesis reactions.

ABSTRACT: Transannular carbonyl-olefin metathesis reactions complement existing procedures for related ring-closing, ring-opening, and intermolecular carbonyl-olefin metathesis. We herein report the development and mechanistic investigation of FeCl₃-catalyzed transannular carbonyl-olefin metathesis reactions that proceed via a distinct reaction path compared to previously reported ring-closing and ring-opening protocols. Specifically, carbonyl-ene and carbonyl-olefin metathesis reaction pathways are competing under FeCl₃-catalysis to ultimately favor metathesis as the thermodynamic product. Importantly, we show that distinct Lewis acid catalysts are able to distinguish between these pathways to enable the selective formation of either transannular carbonyl-ene or carbony

SUBMITTER: Riehl PS 

PROVIDER: S-EPMC6979496 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature