| Abstract
| - The enantioselective Friedel−Crafts addition of a variety of indoles catalyzed by bis(oxazolinyl)pyridine−scandium(III) triflate complexes (Sc(III)−pybox) was accomplished utilizing a series of β-substitutedα,β-unsaturated phosphonates and α,β-unsaturated 2-acyl imidazoles. The acyl phosphonate productswere efficiently transformed into esters and amides, whereas the acyl imidazole adducts were convertedto a broader spectrum of functionalities such as esters, amides, carboxylic acids, ketones, and aldehydes.The sense of stereoinduction and level of enantioselectivity were found to be functions of the size of thesubstrate employed, the substitution on the ligand, and the catalyst loading. Molecular modeling of thecatalyst with the bound substrates was performed based on the crystal structures of the catalyst complexesand the sense of stereoinduction observed in the addition reaction. Nonlinear effects over a range of catalystconcentrations implicate a mononuclear complex as the active catalyst.
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