Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 15, Pages 4973-4977Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201814751
Keywords
asymmetric catalysis; hydrogenation; ketones; manganese; PNN ligands
Categories
Funding
- Ministry of Science and Technology of China [2016YFA0202900]
- National Natural Science Foundation of China [21790333]
- CAS [XDB20000000]
- Youth Innovation promotion Association CAS [2015205]
- Science and Technology Commission of Shanghai Municipality
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A series of Mn-I complexes containing lutidine-based chiral pincer ligands with modular and tunable structures has been developed. The complex shows unprecedentedly high activities (up to 9800 TON; TON=turnover number), broad substrate scope (81 examples), good functional-group tolerance, and excellent enantioselectivities (85-98% ee) in the hydrogenation of various ketones. These aspects are rare in earth-abundant metal catalyzed hydrogenations. The utility of the protocol have been demonstrated in the asymmetric synthesis of a variety of key intermediates for chiral drugs. Preliminary mechanistic investigations indicate that an outer-sphere mode of substrate-catalyst interactions probably dominates the catalysis.
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