Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Biomimetic Platinum-Promoted Polyene Polycyclizations: Influence of Alkene Substitution and Pre-cyclization Conformations

Biomimetic Platinum-Promoted Polyene Polycyclizations: Influence of Alkene Substitution and Pre-cyclization Conformations
Michael J. Geier, Christina H. McCulley, Dean J. Tantillo, Brandi M. Hudson, Michel R. Gagné
Results of kinetic experiments and quantum chemical computations on a series of platinum-promoted polycyclization reactions are described. Analyses of these results reveal a reactivity model that reaches beyond the energetics of the cascade itself, incorporating an ensemble of pre-cyclization conformations of the platinum–alkene reactant complex, only a subset of which are productive for bi- (or larger) cyclization and lead to products. Similarities and differences between this scenario, including reaction coordinates for polycyclization, for platinum- and enzyme-promoted polycyclization reactions are highlighted.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b05381

DOI: 10.1021/jacs.7b05381

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