title: [1H, 13C NMR and stereochemistry studies of 3S-substituted alkoxylquinuclidine by two-dimensional and NOE difference NMR techniques].
abstract: By using optically pure 3S-quinuclidinol, two diastereoisomers (3S-1) and (3S-2) of 3-(substituted) alkoxy-quinuclidine were synthesized. 1H and 13C NMR spectra of (3S-1) and (3S-2) have been completely analyzed utilizing double-quantum filtered COSY, 13C-1H COSY and NOE difference experiment. The NOE difference experiment was used to determine the absolute configuration at C-11 of the diastereomers. According to the results of NOE difference and variable concentration NMR experiments, the configuration about C-11 of (3S-1) is designated as R (1A), whereas the configuration about C-11 of (3S-2) is designated as S (1B). The result was confirmed by X-ray diffraction analysis.
authors.forename: Z C
authors.initials: ZC
authors.lastname: Miao
authors.forename: J H
authors.initials: JH
authors.lastname: Gao
authors.forename: R
authors.initials: R
authors.lastname: Feng
authors.forename: Q K
authors.initials: QK
authors.lastname: Zhang
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010276:Parasympatholytics / Q000032:analysis*; D011812:Quinuclidines / Q000032:analysis*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D010276:Parasympatholytics; D011812:Quinuclidines