Chiral Induction by cinchona alkaloids in the rhodium(II) catalyzed O-H insertion reaction.
Cinchona alkaloids are effective additives for enantioselective O-H insertion of alpha-phenyldiazoacetate and water by rhodium(II) complexes. Addition of silica gel promotes O-H insertion in the reaction rate and the reaction proceeds smoothly at less than the freezing point of water, e.g., -10 degrees C, and provided mandelate in up to 50% ee. The results reported here are the highest asymmetric inductions obtained to date for O-H insertions via a Rh-carbenoid.
Saito
Hiroaki
H
School of Pharmacy, Nihon University. saito.hiroaki@nihon-u.ac.jp
Iwai
Ryo
R
Uchiyama
Taketo
T
Miyake
Muneharu
M
Miyairi
Shinichi
S
D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D056831:Coordination Complexes / Q000737:chemistry*; D015394:Molecular Structure; D010648:Phenylacetates / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D002930:Cinchona Alkaloids; D056831:Coordination Complexes; D010648:Phenylacetates; D014867:Water; D012238:Rhodium