Assignment of the relative and absolute configurations of acyclic secondary 1,2-diols

Shuhei Higashibayashi, Yoshito Kishi

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24 Citations (Scopus)

Abstract

The NMR profiles ( 13C-δ, 1H-δ, 1H(OH)-δ, and 3J H,H) of syn- and anti-diols - 3a,b in achiral solvents were found to be very similar to each other. Contrarily, their Δδ (Δδ=δ (R,R)-2(S,S)-2) behaviors in chiral bidentate NMR solvent (R,R)- and (S,S)-BMBA-p-Me (2) were found to be significantly different. On the basis of this NMR characteristic, a method has been developed to predict both the relative and absolute configurations of acyclic secondary 1,2-diols. Both the relative and absolute configurations of acyclic secondary 1,2-diols can be deduced through analysis of the 13C-Δδ (Δδ=δ (R,R)-2(S,S)-2) behaviors of the two alcoholic carbons in chiral bidentate NMR solvent (R,R)- and (S,S)-BMBA-p-Me (2).

Original languageEnglish
Pages (from-to)11977-11982
Number of pages6
JournalTetrahedron
Volume60
Issue number51
DOIs
Publication statusPublished - 2004 Dec 13
Externally publishedYes

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Keywords

  • Absolute configuration
  • Chiral NMR solvent
  • Diols
  • Relative configuration

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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