Indium(III) Chloride-Promoted Intramolecular Addition of Allylstannanes to Alkynes
- 2 March 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (7) , 2427-2430
- https://doi.org/10.1021/jo035780j
Abstract
In the presence of an equimolar amount of InCl3, 8-tributylstannyl-6-octen-1-ynes (allylstannanes bearing an alkynyl group) were efficiently cyclized to 2-allyl-1-methylenecyclopentanes. In contrast, catalytic use of InCl3 gave 2-allyl-1-(tributylstannylmethylene)cyclopentanes mainly by intramolecular allylstannylation. These cyclizations could proceed via intramolecular addition of an allylindium intermediate.Keywords
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