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Highly Enantioselective Hydrogenation of N ‐Aryl Imines Derived from Acetophenones by Using Ru–Pybox Complexes under Hydrogenation or Transfer Hydrogenation Conditions in Isopropanol
Author(s) -
MenéndezPedregal Estefanía,
Vaquero Mónica,
Lastra Elena,
Gamasa Pilar,
Pizzano Antonio
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405276
Subject(s) - transfer hydrogenation , oxazoline , chemistry , catalysis , aryl , enantioselective synthesis , noyori asymmetric hydrogenation , amine gas treating , denticity , asymmetric hydrogenation , ligand (biochemistry) , pyridine , organic chemistry , combinatorial chemistry , ruthenium , metal , alkyl , biochemistry , receptor
The asymmetric reduction of N ‐aryl imines derived from acetophenones by using Ru complexes bearing both a pybox (2,6‐bis(oxazoline)pyridine) and a monodentate phosphite ligand has been described. The catalysts show good activity with a diverse range of substrates, and deliver the amine products in very high levels of enantioselectivity (up to 99 %) under both hydrogenation and transfer hydrogenation conditions in isopropanol. From deuteration studies, a very different labeling is observed under hydrogenation and transfer hydrogenation conditions, which demonstrates the different nature of the hydrogen source in both reactions.