One-pot sequential Cu-catalyzed reduction and Pd-catalyzed arylation of silyl enol ethers.
[reaction: see text] Enantiomerically enriched beta-substituted diphenylsilyl enol ethers, which can be prepared from Cu-catalyzed asymmetric conjugate reduction, are utilized in the Pd-catalyzed arylation of various aryl bromides. This new method provides a simple route to alpha-arylated cycloalkanones with excellent levels of enantiomeric and diastereomeric purity. The isolation of the intermediate, diphenylsilyl enol ethers is not necessary; the procedure can be carried out in one-pot.
Chae
Junghyun
J
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Yun
Jaesook
J
Buchwald
Stephen L
SL
D000478:Alkylation; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D007659:Ketones; D009942:Organometallic Compounds; D017646:Organosilicon Compounds; D014753:Vinyl Compounds; C100195:vinyl ether; D010165:Palladium; D003300:Copper