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1 H NMR Determination of Absolute Configuration of 1‐ or 2‐Aryl‐Substituted Alcohols and Amines by Means of Their Diastereomers: Novel Separation Technique of Diastereomeric Derivatives of Pyridyl Alcohols by Extraction
Author(s) -
Matsugi Masato,
Itoh Kinuyo,
Nojima Masatomo,
Hagimoto Yuri,
Kita Yasuyuki
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20021216)8:24<5551::aid-chem5551>3.0.co;2-v
Subject(s) - diastereomer , chemistry , aryl , cyclohexanol , absolute configuration , proton nmr , extraction (chemistry) , organic chemistry , catalysis , alkyl
A convenient method to determine the absolute configuration of trans ‐2‐aryl cyclohexanols, 1‐aryl alcohols and amines was achieved. This method takes advantage of the 1 H NMR spectroscopic observations of the remarkable high‐field shift of C18‐CH 3 protons caused by the aromatic shielding effect. It is based on a discrimination of the difference of the environments in two diastereomers derived from 3 β ‐acetoxy‐5‐etienic acid. Furthermore, it was observed that the corresponding diastereomeric derivatives of the pyridyl alcohols were simply separated by extraction based on the difference in their basicity.