Ruthenium-Porphyrin-Catalyzed [4 + 2] Cycloaddition of α,β-Unsaturated Imines and Aldehydes.
A new efficient synthetic route to unsymmetrically substituted dihydropyridine scaffolds via dehydrative [4 + 2] cycloaddition of N-tosylated α,β-unsaturated imines with aldehydes has been developed. This transformation is enabled by (i) the remarkable catalytic ability of the cationic Ru(IV) porphyrin complex to activate both the imino and carbonyl groups and (ii) the hydrophobic nature of the porphyrin ligand, which helps realize robust Lewis acidity in the dehydrative cycloaddition.
Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.
Kazuki
K
Maeda
Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.
Takuma
T
Terada
Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.
Takahiro
T
Iwamoto
Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.|JST, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.
Takuya
T
Kurahashi
Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.
Seijiro
S
Matsubara
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry; D008665:Metalloporphyrins / Q000737:chemistry*; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*
D000447:Aldehydes; D004095:Dihydropyridines; D007097:Imines; D058116:Lewis Acids; D008665:Metalloporphyrins; D012428:Ruthenium