A general synthetic route to differentially functionalized angularly and linearly fused [6-7-5] ring systems: a Rh(I)-catalyzed cyclocarbonylation reaction.
Investigations of a Rh(I)-catalyzed cyclocarbonylation reaction reveal its general synthetic utility for accessing highly functionalized tricyclic [6-7-5] linear and angular ring systems from allene-ynes. Three types of allene-ynes were prepared and subjected to Rh(I)-catalyzed cyclocarbonylation conditions. For three series of allene-ynes, the [6-7-5] ring systems were afforded in varying yields depending on the substrate structure. One series of allene-ynes afforded the [6-6-5] ring system possessing an alpha-alkylidene cyclopentenone as a result of a selective reaction with the proximal double bond of the allene.
Brummond
Kay M
KM
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. kbrummon@pitt.edu
Chen
Daitao
D
Davis
Matthew M
MM
D002384:Catalysis; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*; D012238:Rhodium / Q000737:chemistry*
D011084:Polycyclic Aromatic Hydrocarbons; D012238:Rhodium