H. Brunner et al., Asymmetric catalysis; 138: Synthesis of enantiomerically pure 2-pyridinyl-alpha-ethanols via diastereomeric camphanic esters, SYNTHESIS-S, (11), 2001, pp. 1671-1680
New terdentate facially binding ligands based on the 2-pyridinyl-alpha -eth
anol skeleton were prepared as the racemates. Reaction with the enantiomeri
cally pure (-)-(1S,4R)-camphanoyl chloride gave diastereomeric camphanic es
ters. The pure diastereomers were accessible by separating the diastercomer
ic esters with medium-pressure silica gel chromatography or fractional crys
tallization. X-ray structure analysis of the pure camphanic esters establis
hed the absolute configurations of the 2-pyridinyt-alpha -alcohols. The ena
ntiomerically pure alcohols were obtained after saponification of the diast
ereomerically pure esters.