Asymmetric catalysis; 138: Synthesis of enantiomerically pure 2-pyridinyl-alpha-ethanols via diastereomeric camphanic esters

Citation
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
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
11
Year of publication
2001
Pages
1671 - 1680
Database
ISI
SICI code
0039-7881(200108):11<1671:AC1SOE>2.0.ZU;2-E
Abstract
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.