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Nickel-catalyzed intramolecular [3 + 2 + 2] cycloadditions of alkylidenecyclopropanes. A straightforward entry to fused 6,7,5-tricyclic systems.

Saya L, Fernández I, López F, Mascareñas JL - Org. Lett. (2014)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS) and Departamento de Química Orgánica, Universidad de Santiago de Compostela , 15782 Santiago de Compostela, Spain.

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.

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Calculated Profile for the Reaction of 1l and [Ni(CH2=CH2)2], withor without PMe314
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sch3: Calculated Profile for the Reaction of 1l and [Ni(CH2=CH2)2], withor without PMe314


Nickel-catalyzed intramolecular [3 + 2 + 2] cycloadditions of alkylidenecyclopropanes. A straightforward entry to fused 6,7,5-tricyclic systems.

Saya L, Fernández I, López F, Mascareñas JL - Org. Lett. (2014)

Calculated Profile for the Reaction of 1l and [Ni(CH2=CH2)2], withor without PMe314
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4306596&req=5

sch3: Calculated Profile for the Reaction of 1l and [Ni(CH2=CH2)2], withor without PMe314
Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS) and Departamento de Química Orgánica, Universidad de Santiago de Compostela , 15782 Santiago de Compostela, Spain.

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.

Show MeSH