Nickel-Catalyzed Intramolecular [3 + 2 + 2] Cycloadditions of Alkylidenecyclopropanes. A Straightforward Entry to Fused 6,7,5- Tricyclic Systems

Saya Codesal, LucíaFernández, IsraelMascareñas Cid, José LuisLópez García, Fernando2015-02-192015-02-192014-09-18Saya, L., Fernández, I., López, F., and Mascareñas, J. L. (2014), Nickel-Catalyzed Intramolecular [3 + 2 + 2] Cycloadditions of Alkylidenecyclopropanes. A Straightforward Entry to Fused 6,7,5-Tricyclic Systems. Org. Lett., 2014,16 (19), pp 5008–5011. doi: 10.1021/ol502288x1523-7060E-ISSN 1523-7052http://hdl.handle.net/10347/12377A highly diastereo- and chemoselective intramolecular nickel-catalyzed cycloaddition of alkene- and alkyne-tethered alkynylidenecyclopropanes is reported. The method constitutes the first fully intramolecular [3 + 2 + 2] alkylidenecyclopropropane cycloaddition occurring via a proximal cleavage of the cyclopropane and makes it possible to build relevant 6,7,5-tricyclic frameworks in a single-pot reaction. Importantly, the reaction outcome is highly dependent on the characteristics of the nickel ligands.eng© American Chemical SocietyAlkylidenecyclopropanesCycloadditionsNickelMaterias::Investigación::23 QuímicaNickel-Catalyzed Intramolecular [3 + 2 + 2] Cycloadditions of Alkylidenecyclopropanes. A Straightforward Entry to Fused 6,7,5- Tricyclic Systemsjournal article10.1021/ol502288xopen access