Rhodium(III)-Catalyzed Diastereoselective Synthesis of 1-Aminoindanes via C−H Activation.

The rhodium(III)-catalyzed cross-coupling reaction between N-sulfonyl aldimines and various olefins such as maleimides, fumarates, maleates, α,β-unsaturated ketones, acrylate and nitroalkenes is described. This transformation efficiently leads to the diastereoselective synthesis of pharmacologically privileged 1-aminoindane derivatives via the C−H alkylation followed by subsequent intramolecular cyclization. Notably, single diastereomers in all cases were observed, and the relative stereochemistry of products was confirmed by the X-ray crystallographic data. [ABSTRACT FROM AUTHOR]