Gold(I)-catalysed cycloisomerisation of 1,6-enynes into functionalised allenes.
نویسندگان
چکیده
1,6-Enynes can be transformed into vinylidenecyclopentanes via gold-promoted 5-exo dig cyclisation followed by 1,5-hydride or -alkoxide shift.
منابع مشابه
The role of cyclobutenes in gold(I)-catalysed skeletal rearrangement of 1,6-enynes.
1,6-Enynes with electron-donating substituents at the alkyne undergo gold(I)-catalysed single cleavage skeletal rearrangement, whereas substrates with electron-withdrawing substituents evolve selectively to double cleavage rearrangement. Theoretical calculations provide a qualitative rationale for these effects, and suggest that bicyclo[3.2.0]hept-5-enes are involved as intermediates. We provid...
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The effects of starting material substitution patterns on reaction selectivity for the gold(I)-catalysed cycloisomerisations of aryl substituted 1,7-enynes were investigated. The results indicated the chemoselectivity of the reaction to be highly substrate and catalyst dependent. Either the piperidine or the tetrahydro-1H-azepine product was obtained in moderate to excellent yields depending on...
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X-ray crystal structures of two [(diphosphine)Au2 Cl2 ] complexes (in which diphosphine=P-Phos and xylyl-P-Phos; P-Phos=[2,2',6,6'-Tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine]) were determined and compared to the reported structures of similar atropisomeric gold complexes. Correlations between the Au⋅⋅⋅Au distances and torsional angles for the biaryl series of ligands (MeOBIPHEP, S...
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We have developed gold(I)-catalyzed oxidative cyclopropanation of 1,6-enynes derived from propiolamides employing diphenyl sulfoxide as an oxidant. 1,6-Enynes having a terminal alkyne and a propiolamide tether efficiently transformed into cyclopropane carboxaldehyde derivatives.
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Gold(I)-catalysed tandem oxygen-transfer/cycloisomerisation reaction of 2-(2-propynyl)pyridine N-oxides provides an atom-economical route to indolizinone frameworks.
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عنوان ژورنال:
- Chemical communications
دوره 46 6 شماره
صفحات -
تاریخ انتشار 2010