New phosphine-amino-alcohol tridentate ligands for ruthenium catalyzed asymmetric transfer hydrogenation of ketones

New phosphine-amino-alcohol tridentate ligands (3a-c) and six new ruthenium complexes (4a-c and 5a-c) were synthesized and characterized. Catalytic activities of the metal complexes were tested on aryl alkyl ketones. All of the substrates were converted to related sec-alcohols in excellent yields (up to 99%), but enantioselectivities were insufficient (up to 40% ee). Despite the catalytic performance of 5a-c complexes can be considered as better than 4a-c, actually the catalytic activity of the complexes has been differed according to substrate. The ketones with less positive carbonyl carbons tend to give S-configuration with 5a-c and R-configuration with 4a-c. The catalytic performance of the complexes was rationalized by means of DFT calculations. (C) 2018 Elsevier B.V. All rights reserved.