Catalytic enantioselective Strecker reaction of ketoimines.
A new method for the catalytic enantioselective Strecker reaction (cyanation) of N-diphenylphosphinoyl ketoimines is described. The asymmetric catalyst is a chiral gadolinium complex prepared from Gd(OiPr)3 and the d-glucose-derived ligand 3 in a 1:2 ratio. The reaction has a broad substrate generality, giving high enantioselectivity from aromatic, ethyl, primary alkyl, and alpha,beta-unsaturated ketoimines. The products could be easily converted to disubstituted alpha-amino acids and their derivatives.
Masumoto
Shuji
S
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.
Usuda
Hiroyuki
H
Suzuki
Masato
M
Kanai
Motomu
M
Shibasaki
Masakatsu
M
D002384:Catalysis; D003486:Cyanides / Q000737:chemistry; D005682:Gadolinium / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry; D013237:Stereoisomerism
D003486:Cyanides; D007097:Imines; D009942:Organometallic Compounds; D010720:Phosphines; D005682:Gadolinium