Diastereoselective construction of trans-fused octalone framework via ruthenium-porphyrin-catalyzed cycloaddition.
Lewis acid catalyzed cycloaddition of cyclohexenone and butadiene affords trans-fused octalone with high regio- and diastereoselectivity. The use of the ruthenium porphyrin complex as the Lewis acid catalyst is key to the reaction. The cycloaddition proceeds in toluene with 1 mol % of the ruthenium catalyst at 25 °C.
Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.
Takuma
T
Terada
Takuya
T
Kurahashi
Seijiro
S
Matsubara
D002384:Catalysis; D061565:Cycloaddition Reaction; D003512:Cyclohexanones / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011166:Porphyrins / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003512:Cyclohexanones; D058116:Lewis Acids; D011166:Porphyrins; D012717:Sesquiterpenes; C036468:cyclohexanone; D012428:Ruthenium