NDLI: Metal-Free Intramolecular Carbonyl-Olefin Metathesis of ortho-Prenylaryl Ketones

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Metal-Free Intramolecular Carbonyl-Olefin Metathesis of ortho-Prenylaryl Ketones

Content Provider	Scilit
Author	Schmalz, Hans-Günther Soicke, Arne Slavov, Nikolay Neudörfl, Jörg-Martin
Copyright Year	2011
Description	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.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0030-1260320.pdf
Ending Page	2490
Page Count	4
Starting Page	2487
ISSN	09365214
e-ISSN	14372096
DOI	10.1055/s-0030-1260320
Journal	Synlett
Issue Number	17
Volume Number	2011
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2011-09-19
Access Restriction	Open
Subject Keyword	Journal: Synlett Organic Chemistry Olefin Metathesis Lewis Acids Carbenium Ions Natural Products
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry

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