Ruthenium- and palladium-catalyzed enyne cycloisomerizations: differentially stereoselective syntheses of bicyclic structures.
Enyne cycloisomerizations can provide an efficient means for forming carbon-carbon bonds. We describe stereoselectively dichotomous enyne cycloisomerizations, entirely dependent on the selection of catalytic manifold. Ruthenium catalysis provides trans-fused bicyclic systems, whereas palladium catalysis provides the analogous cis-fused bicycles. A number of substrates are investigated, and the outcomes ultimately offer a clear mechanistic rationale for these observations.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305, USA.
Ferreira
Eric M
EM
Gutierrez
Alicia C
AC
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D010165:Palladium; D012428:Ruthenium