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

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

Organic letters (2014-09-19)

Lucía Saya, Israel Fernández, Fernando López, José L Mascareñas

ABSTRAKT

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.

MATERIAŁY

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Marka

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Sigma-Aldrich

Nickel, nanopowder, <100 nm avg. part. size, ≥99% trace metals basis

Sigma-Aldrich

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Sigma-Aldrich

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Nickel, wire reel, 10m, diameter 0.125mm, annealed, 99.98%

Nickel, wire reel, 0.2m, diameter 0.5mm, as drawn, 99.99+%

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Nickel, foil, 0.5m coil, thickness 0.0125mm, annealed, 99%

Nickel, wire reel, 0.5m, diameter 0.05mm, as drawn, 99.99+%

Nickel, foil, 2m coil, thickness 0.25mm, annealed, 99.98%

Nickel, foil, 0.5m coil, thickness 0.15mm, annealed, 99%

Nickel, wire reel, 100m, diameter 0.5mm, as drawn, 99%

Nickel, foil, 10mm disks, thickness 0.1mm, annealed, 99%

Nickel, foil, 10mm disks, thickness 0.20mm, annealed, 99%

Nickel, foil, 10mm disks, thickness 0.5mm, as rolled, 100%

Nickel, rod, 200mm, diameter 30mm, 99%

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Nickel, rod, 500mm, diameter 20.0mm, 99%

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