title: Catalytic Asymmetric Mannich Reactions with Fluorinated Aromatic Ketones: Efficient Access to Chiral β-Fluoroamines.
abstract: Reported herein is a Zn/Prophenol-catalyzed Mannich reaction using fluorinated aromatic ketones as nucleophilic partners for the direct enantio- and diastereoselective construction of β-fluoroamine motifs featuring a fluorinated tetrasubstituted carbon. The reaction can be run on a gram scale with a low catalyst loading without impacting its efficiency. Moreover, a related aldol reaction was also developed. Together, these reactions provide a new approach for the preparation of pharmaceutically relevant products possessing tetrasubstituted C-F centers.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA). bmtrost@stanford.edu.
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.affiliation: Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA).
authors.forename: Tanguy
authors.initials: T
authors.lastname: Saget
authors.affiliation: Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA).
authors.forename: Andreas
authors.initials: A
authors.lastname: Lerchen
authors.affiliation: Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA).
authors.forename: Chao-I Joey
authors.initials: CI
authors.lastname: Hung
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D007659:Ketones; D005461:Fluorine
keywords: aldol reaction; asymmetric catalysis; enantioselectivity; fluorine; zinc