Dirhodium(II) Tetrakis[N-phthaloyl-(S)-tert-leucinate]: A Notable Catalyst for Enantiotopically Selective Aromatic Substitution Reactions of α-Diazocarbonyl Compounds

Abstract

Dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] catalyzes aromatic substitution reactions of 3-alkyl-substituted 1-diazo-3,3-diphenyl-2-propanones to give (S)-1-alkyl-2-phenyl-2-indanones featured by a chiral quaternary carbon atom in up to 98% ee, the effectiveness of which has been demonstrated by the first enantioselective synthesis of FR115427 [(S)-(+)-1-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride], a non-competitive N-methyl-D-aspartate (NMDA) receptor antagonist.