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.
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.
Kacprzynski
Monica A
MA
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Kazane
Stephanie A
SA
May
Tricia L
TL
Hoveyda
Amir H
AH
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*
D000475:Alkenes; D007659:Ketones; D009942:Organometallic Compounds; D012821:Silanes; C511847:allylsilane; D003300:Copper; D015032:Zinc