Maguire, AR,Buckley, NR,O'Leary, P,Ferguson, G;

1996

November

Chemical Communications

Excellent stereocontrol in intramolecular Buchner cyclisations and subsequent cycloadditions; Stereospecific construction of polycyclic systems

Validated

()

2595

2596

Highly diastereoselective rhodium(II) acetate-catalysed intramolecular addition of alpha-diazo ketones to aromatic rings to form the azulenones 3 has been achieved; the norcaradiene form of 3 undergoes efficient stereospecific cycloaddition with phenyltriazolinedione, in either a stepwise or a tandem process, leading to the pentacyclic systems 4 as a single diastereomer in each case.