Catalytic asymmetric synthesis of alpha-amino phosphonates using enantioselective carbon-carbon bond-forming reactions.
We have developed highly enantioselelctive reactions of silicon enolates with N-acyl-alpha-iminophosphonates leading to optically active alpha-amino phophonates. A copper (II)-diamine complex was shown to be effective in this reaction, and high levels of yield and selectivity were achieved. It is noteworthy that this reaction opens a way to various biologically important, optically active alpha-amino phosphonate derivatives.
Kobayashi
Shu
S
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Kiyohara
Hiroshi
H
Nakamura
Yoshitaka
Y
Matsubara
Ryosuke
R
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D017646:Organosilicon Compounds / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D007097:Imines; D009942:Organometallic Compounds; D063065:Organophosphonates; D017646:Organosilicon Compounds; D003300:Copper