Highly enantioselective hydrogenation of N-unprotected indoles using (S)-C10-BridgePHOS as the chiral ligand

(S)-C-10-BridgePHOS was successfully applied to a highly efficient Pd-catalyzed enantioselective hydrogenation of substituted indoles. The methodology was suitable for the hydrogenation of indoles substituted at the 2-, 3- and 2,3-positions. Products were obtained in quantitative conversion and up to 98% ee. The role the 2-position substituent plays in the hydrogenation process has been proposed. The methodology could be used as an alternative method to synthesize extremely important chiral indolines from N-unprotected indoles. (C) 2013 Elsevier Ltd. All rights reserved.