title: Vicinal functionalization of propiolate esters via catalytic carbocupration: stereoselective formation of substituted vinyl silanes.
abstract: The vicinal functionalization of propiolate esters via a catalytic carbocupration-silicon group migration sequence has been investigated. We have observed that catalyst loadings as low as 5 mol % allow for good yields and excellent diastereoselectivities (>20:1) with a series of Grignard reagents for the synthesis of substituted E-vinyl silanes.
authors.affiliation: Department of Chemistry, The University of Alabama, Tuscaloosa, Alabama 35487-0336, USA.
authors.forename: Amanda J Mueller
authors.initials: AJ
authors.lastname: Hendrix
authors.forename: Michael P
authors.initials: MP
authors.lastname: Jennings
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D004952:Esters; D007202:Indicators and Reagents; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004952:Esters; D007202:Indicators and Reagents; D011422:Propionates; D012821:Silanes; D014753:Vinyl Compounds; D003300:Copper