Asymmetric α-Functionalization of 2-Alkyl Azaarenes: Synthesis of Tertiary Fluorides Having Vicinal Stereogenic Centers
Arko Das, Harshit Joshi, Vinod K. Singh
Abstract
An enantioselective approach for synthesizing fluorinated azaarenes containing vicinal quaternary–tertiary stereocenters is summarized. The chiral copper(I)–phosphine complex binds with the azaarenes followed by Michael addition to unsaturated acyl imidazoles, resulting in α-functionalized products with an excellent level of enantioselectivities (up to 99%), diastereoselectivities (>20:1), and yields (up to 97%). Furthermore, post-functionalization of the acyl imidazole part has also been demonstrated.
Topics & Concepts
StereocenterVicinalChemistryEnantioselective synthesisSurface modificationAlkylPhosphineImidazoleCombinatorial chemistryOrganic chemistryCatalysisPhysical chemistryFluorine in Organic ChemistryAsymmetric Synthesis and CatalysisSynthesis and Catalytic Reactions