American Chemical Society
ol5b02654_si_001.pdf (26.62 MB)

Ruthenium-Porphyrin-Catalyzed [4 + 2] Cycloaddition of α,β-Unsaturated Imines and Aldehydes

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journal contribution
posted on 2015-11-06, 00:00 authored by Kazuki Maeda, Takuma Terada, Takahiro Iwamoto, Takuya Kurahashi, Seijiro Matsubara
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.