Journal
SYNLETT
Volume -, Issue 17, Pages 2487-2490Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1260320
Keywords
olefin metathesis; cyclization; Lewis acids; carbenium ions; oxetanes; natural products
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Funding
- University of Cologne
- Fonds der Chemischen Industrie
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On treatment with boron trifluoride etherate as a Lewis acid, acetophenone and benzophenone derivatives bearing a prenyl (or a related) side chain in ortho-position were shown to undergo intramolecular carbonyl-olefin metathesis, in the absence of any transition-metal catalyst. The cationic cyclization process is supposed to proceed via an oxetane intermediate, which fragments to give the cyclization product (indene or 1,2-dihydronaphthalene) and a ketone (acetone) as a stoichiometric by-product. Several substrates were shown to afford the metathesis products with up to 93% yield.
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