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Determination of absolute configurations of β- or γ-methyl substituted secondary alcohols by NMR spectroscopy

✍ Scribed by Haruko Takahashi; Makoto Iwashima; Kazuo Iguchi

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
228 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new method has been developed for determining the absolute configurations of acyclic [5-or ~--methyl substituted secondary alcohols using their 2NMA esters. The 1H-NMR spectra of (R)-and (S)-2NMA esters of model compounds were measured, and A6 values (6R.este r --6S_este r) for the corresponding protons were compared between syn and anti compounds. Threshold values important for judging the relative stereoehemistry of the two chiral centers bearing methyl and hydroxy groups were obtained. The absolute configuration of the chiral omter bearing a secondary hydroxy group is easily determined based on the sign of A6 values as in the MTPA method and thus in the present study it was also possible to clearly determine the absolute configuration of the chiral center bearing a methyl group.

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