Rapid synthesis of medium-ring fused polycarbocyclic systems by rearrangement of carbenoid-derived oxonium ylides

J. Stephen Clark, Carine Guérot, Claire Wilson, Alexander J. Blake
2007 Chemical Communications  
General procedure for rhodium(II) acetate catalysed ylide formation and rearrangement. A solution of the α-diazo ketone (0.46 mmol) in CH 2 Cl 2 (60 mL) was added dropwise over 1.25 h to a stirred solution of rhodium(II) acetate dimer (2 mol%, 9 μmol) in CH 2 Cl 2 (45 mL) at room temperature under an atmosphere of argon. After addition was complete, the reaction mixture was concentrated in vacuo to give a green oil and the crude product was then purified by flash column chromatography on silica
more » ... gel. General procedure for copper(II) hexafluoroacetylacetonate catalysed ylide formation and rearrangement. A solution of the α-diazo ketone (0.46 mmol) in CH 2 Cl 2 (60 mL) was added dropwise over 1 h to a stirred solution of copper(II) hexafluoroacetylacetonate (2 mol%, 9 μmol) in CH 2 Cl 2 (45 mL) heated at reflux under an atmosphere of argon. After addition was complete, the reaction mixture was stirred for a further 30 min. Then the reaction mixture was concentrated in vacuo to a green oil and then purified by flash column chromatography.
doi:10.1039/b709064a pmid:17925953 fatcat:o6m2wehb4rd4bgqjkrj6obwi6i