title: Enantioselective redox-relay oxidative heck arylations of acyclic alkenyl alcohols using boronic acids.
abstract: A general, highly selective asymmetric redox-relay oxidative Heck reaction using achiral or racemic acyclic alkenols and boronic acid derivatives is reported. This reaction delivers remotely functionalized arylated carbonyl products from acyclic alkenol substrates, with excellent enantioselectivity under mild conditions, bearing a range of useful functionality. A preliminary mechanistic investigation suggests that the regioselectivity of the initial migratory insertion is highly dependent on the electronic nature of the boronic acid and more subtle electronic effects of the alkenyl alcohol.
authors.affiliation: Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, United States.
authors.forename: Tian-Sheng
authors.initials: TS
authors.lastname: Mei
authors.forename: Erik W
authors.initials: EW
authors.lastname: Werner
authors.forename: Alexander J
authors.initials: AJ
authors.lastname: Burckle
authors.forename: Matthew S
authors.initials: MS
authors.lastname: Sigman
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D001897:Boronic Acids; D007659:Ketones