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The Role of Attractive van der Waals Forces in the Catalysis of Michael Addition by a Phenyl Decorated Uranyl-Salophen Complex

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journal contribution
posted on 05.12.2008, 00:00 by Antonella Dalla Cort, Luigi Mandolini, Luca Schiaffino
The Et3N-assisted addition of β-ketoester 3 to MVK in chloroform is catalyzed with high turnover efficiency by the phenyl-substituted uranyl−salophen compound 2b but not by the parent compound 1b. A plausible mechanism is suggested, involving concomitant nucleophilic attack at the β-carbon and hydrogen bonding between the Et3NH+ countercation and the carbonyl oxygen of the s-cis conformation of the enone reactant. The role of the van der Waals interactions with the aromatic side arm of 2b as a crucial driving force for catalysis is discussed.