The synthesis of chiral indanones, and its interesting chiral variant tetralone, are used as a backbone in pharmaceutical preparations to treat diseases ranging from Alzheimer’s disease to hypertension, as well as far-ranging uses in the food science crop industry. Cationic chelating rhodium catalysts have been shown to be effective in the low-energy high-yield formation of related cyclic ketones, and our computational work helps explain numerous aspects of the hydroacylation reaction mechanism. Bifurcating to produce indanone and tetralone products, the indanone formation involves a single vinylbenzaldehyde substrate molecule, whereas the tetralone product is afforded by the dimerization of two of the substrate molecules. The application of the computational methods and parameters in the form of density functionals, solvent environments, and basis sets demand that care be taken to accurately reflect the nature and characteristics of the reaction pathway.

Modeling rhodium-catalyzed hydroacylation of formylstyrene: Competitive formation of indanone and tetralone products

253rd National Meeting (2017)

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