( S)-1-Aminoindane: synthesis by chirality transfer using ( R)-phenylglycine amide as chiral auxiliary

Abstract

A practical asymmetric synthesis of nearly enantiomerically pure ( S)-1-aminoindane has been developed. The key step involves the diastereoselective heterogeneous metal-catalyzed reduction of the ketimine of 1-indanone with the chiral auxiliary ( R)-phenylglycine amide. The selectivity of the asymmetric hydrogenation step was optimized with regard to metal catalyst, solvent and catalyst loading. The chiral auxiliary was removed by means of a novel non-reductive procedure. Thus, ( S)-1-aminoindane with an ee of 96% was prepared in 58% overall yield from ( R)-phenylglycine amide in an effective three-step procedure.