Remote chirality transfer in nucleophilic catalysis with N-(4-pyridinyl)-L-proline derivatives.
Chiral nucleophilic catalysts 5-15 were prepared starting from L-proline. Catalysts 9 and 14 promoted acylative kinetic resolution of racemic amino alcohol derivative 16 with selectivity factors of 8.1 and 11, respectively, at ambient temperature. Since chiral elements are not present in the catalytically active pyridine ring in these catalysts, chirality transfer from the remote stereogenic center to the reactive site (N-acylpyridinium) is suggested to be responsible for the differentiation between enantiomers.
Kawabata
Takeo
T
Institute for Chemical Research, Kyoto University, Uji, Kyoto, Japan. kawabata@scl.kyoto-u.ac.jp
Stragies
Roland
R
Fukaya
Takayuki
T
Fuji
Kaoru
K
D000215:Acylation; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
D011725:Pyridines; D011392:Proline