2-fluoro-2-phenylacetic acid as a chiral derivatizing agent .6. Distinction of configurations of its esters with 2,2'-dihydroxy-1,1'-binaphthyl and some derivatives by F-19 NMR

The title compound was found to be useful as a chiral derivating agent in F-19 NMR spectroscopy, to determine the enantiomeric purity of 2,2'-dihydroxybinaphtyl and its monoether derivatives. The configurations of ether derivatives are easily deduced from that of known binaphthol, and a straightforward relationship is established between the configurations of the ethers and the delta F chemical shifts. A molecular modelling analysis is consistent with the experimental and NMR results. Copyright (C) 1996 Elsevier Science Ltd