Ruthenium-Catalyzed Cycloaddition between Propargylic Alcohols and Cyclic 1,3-Dicarbonyl Compounds via an Allenylidene Intermediate
- 14 April 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (10), 3408-3412
- https://doi.org/10.1021/jo0357465
Abstract
Thiolate-bridged diruthenium complexes such as [Cp*RuCl(μ2-SR)2RuCp*Cl] (Cp* = η5-C5Me5; R = Me, nPr, iPr) and [Cp*RuCl(μ2-SiPr)2RuCp*(OH2)]OTf (OTf = OSO2CF3) promote the cycloaddition between propargylic alcohols and cyclic 1,3-dicarbonyl compounds to give either the corresponding 4,6,7,8-tetrahydrochromen-5-ones or 4H-cyclopenta[b]pyran-5-ones in high yields with complete regioselectivity. This catalytic cycloaddition provides a simple and one-pot synthetic protocol for a variety of substituted chromenones and cyclopenta[b]pyranones.Keywords
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