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

  • Takahashi H
  • Iwashima M
  • Iguchi K
  • 4


    Mendeley users who have this article in their library.
  • 7


    Citations of this article.


A new method has been developed for determining the absolute configurations of acyclic β- or γ-methyl substituted secondary alcohols using their 2NMA esters. The1H-NMR spectra of (R)- and (S)-2NMA esters of model compounds were measured, and Δδ values (δ(R-ester) - δ(S-ester) for the corresponding protons were compared between syn and anti compounds. Threshold values important to judging the relative stereochemistry of the two chiral centers bearing methyl and hydroxy groups were obtained. The absolute configuration of the chiral bearing a secondary hydroxy group is easily determined based on the sign of Δδ 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.

Author-supplied keywords

  • Alcohol
  • Configuration
  • NMR
  • Stereochemistry

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document


  • Haruko Takahashi

  • Makoto Iwashima

  • Kazuo Iguchi

Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free