title: Cu-catalyzed asymmetric conjugate additions of dialkyl- and diarylzinc reagents to acyclic beta-silyl-alpha,beta-unsaturated ketones. Synthesis of allylsilanes in high diastereo- and enantiomeric purity.
abstract: A readily available and simple (MW = 444.5 g/mol) valine-based chiral phosphine is used to promote highly efficient catalytic asymmetric conjugate additions of dialkyl- and diarylzinc reagents to acyclic beta-silyl-alpha,beta-unsaturated ketones. The catalytic asymmetric protocol allows access to versatile allylsilanes that bear a trisubstituted olefin in high diastereo- and enantiomeric purity.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
authors.forename: Monica A
authors.initials: MA
authors.lastname: Kacprzynski
authors.forename: Stephanie A
authors.initials: SA
authors.lastname: Kazane
authors.forename: Tricia L
authors.initials: TL
authors.lastname: May
authors.forename: Amir H
authors.initials: AH
authors.lastname: Hoveyda
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D000475:Alkenes; D007659:Ketones; D009942:Organometallic Compounds; D012821:Silanes; C511847:allylsilane; D003300:Copper; D015032:Zinc