title: (Z)-alpha-haloacrylates: an exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates.
abstract: (Z)-alpha-Fluoro-, (Z)-alpha-chloro-, and (Z)-alpha-bromoacrylates were obtained with unprecedented yield and stereocontrol (>99%) via addition of the corresponding commercial trihaloacetates to aldehydes at room temperature using stoichiometric Cr(II) salts or catalytic Cr(II) with a regeneration system. The intermediate 2,2-dihalo-3-hydroxy adducts could be isolated in good yields under conditions of limited reagent at 0 degrees C.
authors.affiliation: Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, TX 75390-9038, USA.
authors.forename: D K
authors.initials: DK
authors.lastname: Barma
authors.forename: Abhijit
authors.initials: A
authors.lastname: Kundu
authors.forename: Hongming
authors.initials: H
authors.lastname: Zhang
authors.forename: Charles
authors.initials: C
authors.lastname: Mioskowski
authors.forename: J R
authors.initials: JR
authors.lastname: Falck
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000179:Acrylates / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis*; D002857:Chromium / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000179:Acrylates; D000447:Aldehydes; D000475:Alkenes; D006846:Hydrocarbons, Halogenated; D002857:Chromium