Ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation and 1,3-dipolar cycloaddition reactions of alpha-diazo ketones.
[reaction: see text] The ruthenium porphyrin-catalyzed reactions of diazo ketones with pi-unsaturated compounds via carbonyl ylide formation/cycloaddition cascade exhibit product yields and selectivities comparable to the analogous reactions with dirhodium carboxylates as catalysts. By grafting a ruthenium porphyrin on poly(ethylene glycol) (Zhang, J.-L.; Che, C.-M. Org. Lett. 2002, 4, 1911), a recyclable catalytic system is developed with over 5700 product turnovers attained for the reaction of 1-diazo-2,5-hexanedione with dimethyl acetylenedicarboxylate.
Zhou
Cong-Ying
CY
Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong.
Yu
Wing-Yiu
WY
Che
Chi-Ming
CM