185674-71-9Relevant academic research and scientific papers
Stereocontrol in the intramolecular Buchner reaction of diazoketones
Maguire, Anita R.,Buckley, N. Rachael,O'Leary, Patrick,Ferguson, George
, p. 4077 - 4091 (2007/10/03)
Rhodium(II) acetate catalysed intramolecular Buchner cyclisation of a series of diazoketones 1 proceeds with excellent diastereoselectivity to produce the trans substituted azulenones 2, which exist as a rapidly equilibrating cycloheptatriene-norcaradiene system, from which the norcaradiene tautomers can be efficiently trapped as PTAD cycloadducts 4. The cyclisation-cycloaddition sequence can be conducted in either a stepwise or a tandem process, leading to the pentacyclic systems 4 as a single diastereomer in each case. In the reaction of diazoketone If intramolecular cyclopropanation competes with cyclisation to the aromatic ring.
Excellent stereocontrol in intramolecular Buchner cyclisations and subsequent cycloadditions; stereospecific construction of polycyclic systems
Maguire, Anita R.,Buckley, N. Rachael,O'Leary, Patrick,Ferguson, George
, p. 2595 - 2596 (2007/10/03)
Highly diastereoselective rhodium(II) acetate-catalysed intramolecular addition of α-diazo ketones to aromatic rings to form the azulenones 3 has been achieved; the norcaradiene form of 3 undergoes efficient stereospecific cycloaddition with phenyltriazol
