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Journal of Chemical Crystallography

, Volume 41, Issue 3, pp 338–342 | Cite as

Absolute Configuration Determination of Two Optically Active Cyclopropyl-Ketoacids: (1′S, 3S) 3-(2′,2′-Dichloro-1′-methyl-cyclopropyl)-6-oxo-heptanoic acid and (1′S, 3S) 3-(2′,2′-Dibromo-1′-methyl-cyclopropyl)-6-oxo-heptanoic acid

  • Hossni Ziyat
  • Moulay Youssef Ait Itto
  • Mustapha Ait Ali
  • Abdellah Karim
  • Abdelkhalek Riahi
  • Jean-Claude Daran
ORIGINAL PAPER

Abstract

The title compounds C11H16Cl2O3 (III) and C11H16Br2O3 (IV) have been prepared from (S)-Limonen. Their crystal structure and absolute configuration have been determined by X-ray analysis which confirmed the 1′S absolute configuration at the cyclopropyl moiety, in agreement with the known absolute configuration of the starting material. Both (III) and (IV) are orthorhombic, space group P212121 with a = 7.2558(4) Å (for III) 7.4058(6) Å (for IV), b = 9.7885(5) Å (for III) 9.7459(7) Å (for IV), c = 17.7551(10) Å (for III) 18.0354(14) Å (for IV), α = 90°, β = 90°, γ = 90° and Z = 4.

Graphical Abstract

Absolute configuration determination, via an X-ray crystallographic study, of two optically active cyclopropyl-ketoacids.

Keywords

Cyclopropyl-ketoacids (S)-Limonene Cyclopropanation Oxidative cleavage X-ray analysis 

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Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Hossni Ziyat
    • 1
  • Moulay Youssef Ait Itto
    • 1
  • Mustapha Ait Ali
    • 1
  • Abdellah Karim
    • 1
  • Abdelkhalek Riahi
    • 2
  • Jean-Claude Daran
    • 3
  1. 1.Laboratoire des Substances Naturelles et des HétérocyclesDépartement de Chimie, Faculté des Sciences-SemlaliaMarrakechMarocco
  2. 2.UMR 6519 “Réactions Sélectives et Applications”, Université de Reims Champagne-Ardenne, Faculté des SciencesReims Cedex 2France
  3. 3.Laboratoire de Chimie de CoordinationUFR CNRS 8241Toulouse CedexFrance

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