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Structural Chemistry

, Volume 6, Issue 3, pp 191–195 | Cite as

Synthesis and structural characterization of camphanates of (−)-(2S3S,3S) and (+)-(2S,3R)-4-Phenyl-3-bromo-2-butanol diastereoisomers

  • Alain Carpy
  • Jean -Michel Léger
  • Danielle Roche
  • Michel P. Madesclaire
  • Pascale Besse
  • Henri Veschambre
Article
  • 28 Downloads

Abstract

The X-ray crystal structures of (−)-syn-4-phenyl-3-bromo-2-butyl camphanate (I) and (+-anti-4-phenyl-3-bromo-2-butyl camphanate (II) have been determined. Thesyn diastereoisomer of bromohydrin has the (2S,3S) absolute configuration whereas theanti diastereoisomer has the (2S,3R) absolute configuration. The crystallized derivatives I and II have been obtained by the reaction of each stereoisomer of bromohydrin, synthesized by reduction with baker's yeast, with (1S)-camphanic chloride. Crystal data: (I) C20H25BrO4:Mw: 409.32; orthorhombic,P212121;a=11.245(3),b=12.086(1),c=14.512(4) å; Z=4; finalR=0.053 for 1819 observed reflections. (II) C20H25BrO4;Mw=409.32; monoclinic, P21;a=11.352(1),b=6.378(1),c=14.255(2) å,Β=110.38(1)ℴ;Z=2; finalR=0.045 for 1672 observed reflections.

Key words

Chiral bromohydrins syn- andanti-diastereoisomer chemoenzymatic synthesis X-ray crystallography absolute configuration 

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Copyright information

© Plenum Publishing Corporation 1995

Authors and Affiliations

  • Alain Carpy
    • 3
  • Jean -Michel Léger
    • 3
  • Danielle Roche
    • 1
  • Michel P. Madesclaire
    • 1
  • Pascale Besse
    • 2
  • Henri Veschambre
    • 2
  1. 1.Groupe de Recherche en Pharmacochimie, U.F.R. de PharmacieUniversité d'AuvergneClermont-Ferrand Cedex 1France
  2. 2.Laboratoire de Chimie Organique Biologique, URA 485 CNRSUniversité Blaise-PascalAubière CedexFrance
  3. 3.Laboratoire de Chimie AnalytiqueUniversité de Bordeaux IIBordeaux CedexFrance

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