Synthesis of chiral aminophosphines via nucleophilic aromatic substitution and their application to palladium-catalyzed enantioselective allylic substitution.
Novel chiral aminophosphines, N,N-disubstituted diphenyl(1-amino-2-naphthyl)phosphines 4 were synthesized via nucleophilic aromatic substitution reaction on 1-methoxy-2-(diphenylphosphinoyl)naphthalene (1) by chiral lithium amides 2, followed by reduction of the phosphinoyl function. The new ligands were tested for their efficiency in the palladium-catalyzed allylic substitution of dimethyl malonate with 1,3-diphenyl-2-propenyl acetate and high asymmetric inductions up to 80%ee were observed.
Hattori
T
T
Department of Biochemistry and Engineering, Faculty of Engineering, Tohoku University, Sendai, Japan.
Komuro
Y
Y
Hayashizaka
N
N
Takahashi
H
H
Miyano
S
S
D000498:Allyl Compounds / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium / Q000737:chemistry; D010720:Phosphines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000498:Allyl Compounds; D001555:Benzene Derivatives; D010720:Phosphines; D010165:Palladium