Stereochemistry study of 3R-substituted alkoxyl-quinuclidine

Abstract

By using optically pure 3(R)-quinuclidinol, two diastereoisomers I and II of 3-(substituted) alkoxyl-quinuclidine were synthesized. 1H and 13C NMR spectra of I and II have been completely analyzed utilizing double-quantum filtered COSY, 13C-1H COSY and NOE difference experiment The NOE difference experiment is used to determine the absolute configuration at 11-C of the diastereomers. According to the results of NOE difference and variable concentration NME experiments, the configuration about 11-C of I is designated as S, whereas the configuration about 11-C of II is designated as R. The result was confirmed by X-ray diffraction anal.

Key words: ALKOXYL GROUP, NMR SPECTROMETRY, TWO-DIMENSIONAL, STEREOCHEMISTRY, SPATIAL STRUCTURE, QUINUCLIDINE P, SUBTRACTION SPECTRA

CLC Number:

O621
R97

Cite this article

MIU ZHENCHUN;GAO JIANHUA;FENG RUI;ZHANG QIKAI. Stereochemistry study of 3R-substituted alkoxyl-quinuclidine[J]. Acta Chimica Sinica, 1990, 48(3): 302-306.

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