Nickel-Catalyzed Intramolecular [3 + 2 + 2] Cycloadditions of Alkylidenecyclopropanes. A Straightforward Entry to Fused 6,7,5- Tricyclic Systems
Loading...
Identifiers
Publication date
Advisors
Tutors
Editors
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
Metrics
Export
Abstract
A 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.
Description
Keywords
Bibliographic citation
Saya, 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/ol502288x
Relation
Has part
Has version
Is based on
Is part of
Is referenced by
Is version of
Requires
Publisher version
http://dx.doi.org/10.1021/ol502288xSponsors
This work was supported by the Spanish MINECO (SAF2010-20822-C02-01/02, CTQ2010-20714-C02-01/BQU, CTQ2013-44303-P and CSD2007-00006, Consolider-Ingenio), the ERDF, the Xunta de Galicia (GRC2010/12, GR2013-041, INCITE09 209084PR), and the ERC (Adv. Grant. 340055). We thank Dr. G. Bhargava (Punjab Technical University) for initial work and the Orfeo-Cinqa network.
Rights
© American Chemical Society