100613-11-4Relevant articles and documents
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.