title: Stereoselective syntheses of trisubstituted olefins via platinum catalysis: alpha-silylenones with geometrical complementarity.
abstract: The stereoselective syntheses of alpha-silylenones using catalytic PtCl(2) are reported. Via alkyne activation, alpha-hydroxypropargylsilanes are converted to (Z)-silylenones through a highly selective silicon migration. The complementary (E)-silylenones are accessed by a regioselective hydrosilylation of the ynone precursor. The synthetic utility of these compounds is demonstrated in cross-coupling reactions, highlighting the potential of these protocols for the syntheses of geometrically defined trisubstituted olefins.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Rooke
authors.forename: Eric M
authors.initials: EM
authors.lastname: Ferreira
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010984:Platinum / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000480:Alkynes; D012821:Silanes; D010984:Platinum