Asymmetric Synthesis of Fluorophenylalanines and (Trifluoromethyl)phenylalanines; the Use of Chiral Pyridoxamine-Like Pyridinophane-Zinc Complex as an Enzyme Mimic
- 1 July 1990
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 63 (7), 1925-1928
- https://doi.org/10.1246/bcsj.63.1925
Abstract
Transamination reactions in the presence of zinc(II) ion between (R)- or (S)-15-aminomethyl-14-hydroxy-5,5-dimethyl-2,8-dithia[9](2,5)pyridinophane, pyridoxamine analog with planar chirality, and o-, m-, and p-fluorophenylpyruvic acids or o-, m-, and p-(trifluoromethyl)phenylpyruvic acids gave the corresponding fluorophenylalanines or (trifluoromethyl)phenylalanines with 33–66% enantiomeric excess in moderate yields. The observed rate constants of these transaminations, kobsd, were determined with a concomitant observation of of a linear relationship between logkobsd and Hammett’s constant, σ0.Keywords
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