title: Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters.
abstract: The copper-catalyzed diboration of ketones followed by an acid-catalyzed elimination leads to the formation of 1,1-disubstituted and trisubstituted vinyl boronate esters with moderate to good yields and selectivity. Addition of tosic acid to the crude diboration products provides the corresponding vinyl boronate esters upon elimination. The trisubstituted vinyl boronate esters are formed as the (Z)-olefin isomer, which was established by subjecting the products to a Suzuki-Miyaura coupling reaction to obtain alkenes of known geometry.
authors.affiliation: Department of Chemistry and Biochemistry, University of San Diego , 5998 Alcala Park, San Diego, California 92110, United States.
authors.forename: Weiye
authors.initials: W
authors.lastname: Guan
authors.forename: Alicia K
authors.initials: AK
authors.lastname: Michael
authors.forename: Melissa L
authors.initials: ML
authors.lastname: McIntosh
authors.forename: Liza
authors.initials: L
authors.lastname: Koren-Selfridge
authors.forename: John P
authors.initials: JP
authors.lastname: Scott
authors.forename: Timothy B
authors.initials: TB
authors.lastname: Clark
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D001897:Boronic Acids; D007659:Ketones; D014753:Vinyl Compounds; C519434:vinylboronate ester; D003300:Copper