title: Scalable methodology for the catalytic, asymmetric alpha-bromination of acid chlorides.
abstract: The optimization of a practical, catalytic, asymmetric process for the alpha-bromination of acid chlorides to produce synthetically versatile, optically active alpha-bromoesters is reported. A range of products is produced in high enantioselectivity and moderate to good chemical yields with retention of both upon scale-up. The reactions herein are catalyzed by cinchona alkaloid derivatives, with the best performance achieved by the use of a proline cinchona alkaloid conjugate designed in a de novo fashion.
authors.affiliation: Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
authors.forename: Cajetan
authors.initials: C
authors.lastname: Dogo-Isonagie
authors.forename: Tefsit
authors.initials: T
authors.lastname: Bekele
authors.forename: Stefan
authors.initials: S
authors.lastname: France
authors.forename: Jamison
authors.initials: J
authors.lastname: Wolfer
authors.forename: Anthony
authors.initials: A
authors.lastname: Weatherwax
authors.forename: Andrew E
authors.initials: AE
authors.lastname: Taggi
authors.forename: Thomas
authors.initials: T
authors.lastname: Lectka
mesh_terms: D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004952:Esters; D006843:Hydrocarbons, Chlorinated; D001966:Bromine