title: Copper-catalyzed asymmetric hydrogenation of aryl and heteroaryl ketones.
abstract: High throughput screening enabled the development of a Cu-based catalyst system for the asymmetric hydrogenation of prochiral aryl and heteroaryl ketones that operates at H2 pressures as low as 5 bar. A ligand combination of (R,S)-N-Me-3,5-xylyl-BoPhoz and tris(3,5-xylyl)phosphine provided benzylic alcohols in good yields and enantioselectivities. The electronic and steric characteristics of the ancillary triarylphosphine were important in determining both reactivity and selectivity.
authors: Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA.
authors: Scott W
authors: SW
authors: Krabbe
authors: Mark A
authors: MA
authors: Hatcher
authors: Roy K
authors: RK
authors: Bowman
authors: Mark B
authors: MB
authors: Mitchell
authors: Michael S
authors: MS
authors: McClure
authors: Jeffrey S
authors: JS
authors: Johnson
mesh_terms: D001592:Benzyl Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D006865:Hydrogenation; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001592:Benzyl Alcohols; D007659:Ketones; D008024:Ligands; D010720:Phosphines; D003300:Copper; C044646:phosphine