title: Regioselective derivatizations of a tribrominated atropisomeric benzamide scaffold.
abstract: The enantioselective synthesis of atropisomeric, tribrominated benzamides and subsequent regioselective transformations to afford derivatized, axially chiral molecules is reported. The enantioenriched tribromides were carried through sequential Pd-catalyzed cross-coupling and lithium-halogen exchange with high regioselectivity and enantioretention. A variety of complexity-generation functional group installations were performed to create a library of homochiral benzamides. The potential utility of these molecules is demonstrated by using a phosphino benzamide derivative as an asymmetric ligand in a Pd-catalyzed allylic alkylation.
authors.affiliation: Department of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.
authors.forename: Kimberly T
authors.initials: KT
authors.lastname: Barrett
authors.forename: Scott J
authors.initials: SJ
authors.lastname: Miller
mesh_terms: D000478:Alkylation; D001549:Benzamides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001549:Benzamides; D006842:Hydrocarbons, Brominated; D010165:Palladium