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new class of Lewis acid-catalyzed carbonyl-olefin metathesis reactions is
described that complements existing protocols for related ring-closing,
ring-opening, and intermolecular transformations. These transannular
carbonyl-olefin metathesis reactions rely on FeCl3 as an inexpensive
Lewis acid catalyst and are mechanistically distinct from previously developed
protocols for ring closing, ring-opening and intermolecular metathesis.
Specifically, carbonyl-ene and carbonyl-olefin metathesis reaction paths are
competing to ultimately favor metathesis as the thermodynamic product.
Importantly, we show that distinct Lewis acid catalysts are able to
differentiate between these pathways to enable the selective formation of
transannular carbonyl-ene or carbonyl-olefin metathesis products thus providing
a valuable approach to the molecular editing of naturally occurring complex
molecules. Additionally, these results are expected to enable further advances
in catalyst design for carbonyl-olefin metathesis to ultimately develop
efficient and high-yielding catalytic carbonyl olefination reactions.