TY  - JOUR
  - Maguire, AR,Buckley, NR,O'Leary, P,Ferguson, G
  - 1998
  - July
  - Rna-A Publication of The Rna Society
  - Stereocontrol in the intramolecular Buchner reaction of diazoketones
  - Validated
  - ()
  - ARYL DIAZOKETONES RHODIUM(II)-CATALYZED DECOMPOSITION DIAZOMETHYL KETONES EFFICIENT SYNTHESIS DIAZO KETONES CYCLOHEPTATRIENE ALPHA NORCARADIENE CYCLOADDITION CYCLIZATION
  - 4077
  - 4091
  - 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 1 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.
DA  - 1998/07
ER  - 

@article{V43339467,
   = {Maguire,  AR and Buckley,  NR and O'Leary,  P and Ferguson,  G },
   = {1998},
   = {July},
   = {Rna-A Publication of The Rna Society},
   = {Stereocontrol in the intramolecular Buchner reaction of diazoketones},
   = {Validated},
   = {()},
   = {ARYL DIAZOKETONES RHODIUM(II)-CATALYZED DECOMPOSITION DIAZOMETHYL KETONES EFFICIENT SYNTHESIS DIAZO KETONES CYCLOHEPTATRIENE ALPHA NORCARADIENE CYCLOADDITION CYCLIZATION},
  pages = {4077--4091},
   = {{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 1 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.}},
  source = {IRIS}
}