Highly Enantioselective Direct Asymmetric Reductive Amination of 2-Acetyl-6-Substituted Pyridines
Masatoshi Yamada, Kazuki Azuma, Mitsuhisa Yamano
Abstract
A highly direct asymmetric reductive amination of a variety of ketone substrates, including 2-acetyl-6-substituted pyridines, β-keto esters, β-keto amides, and 1-(6-methylpyridin-2-yl)propan-2-one, has been disclosed for the first time (94.6% to >99.9% ee). With ammonium trifluoroacetate as the nitrogen source, various chiral corresponding primary amines were prepared in excellent enantioselectivity and conversion in the presence of a commercially available and inexpensive chiral catalyst, Ru(OAc)2{(S)-binap}, under 0.8 MPa of hydrogen gas pressure.
Topics & Concepts
ChemistryReductive aminationEnantioselective synthesisCatalysisAminationKetoneBINAPAmmoniumOrganic chemistryHydrogenCombinatorial chemistryMedicinal chemistryAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisAdvanced Synthetic Organic Chemistry