Catalytic asymmetric conjugate addition of dialkylzinc reagents to beta-aryl-alpha,beta-unsaturated N-2,4,6-triisopropylphenylsulfonylaldimines with use of N-Boc-L-Val-connected amidophosphane-copper(I) catalyst.
Asymmetric conjugate addition of dialkylzinc to alpha,beta-unsaturated N-2,4,6-triisopropylphenylsulfonylaldimines 9 was catalyzed by 5 mol % N-Boc-L-valine-connected amidophosphane 5a-Cu(MeCN)(4)BF(4) in the presence of 4 angstroms MS in toluene to afford, after hydrolysis of an imine to an aldehyde through a short alumina column and reduction with sodium borohydride, the corresponding beta-alkylated alkanols 10 with 67-91% ee in reasonably high yields.
Soeta
Takahiro
T
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Kuriyama
Masami
M
Tomioka
Kiyoshi
K
D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003300:Copper / Q000737:chemistry*; D006868:Hydrolysis; D007097:Imines / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D014633:Valine / Q000737:chemistry; D015032:Zinc / Q000737:chemistry
D007097:Imines; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D009943:Organophosphorus Compounds; D003300:Copper; D014633:Valine; D015032:Zinc