Journal of Chemical Crystallography

, Volume 42, Issue 9, pp 911–915

Synthesis and Structure of 2-Cyclohexylamino-3-methyl-1,1-diphenyl-butan-1-ol (d-N-Cyclohexyl-diphenylvalinol), an Amino Alcohol Ligand Useful in Asymmetric Catalysis

  • Eric W. Reinheimer
  • A. J. Hickman
  • J. E. Moretti
  • X. Ouyang
  • Katherine A. Kantardjieff
  • Adam R. Johnson
Original Paper

DOI: 10.1007/s10870-012-0334-5

Cite this article as:
Reinheimer, E.W., Hickman, A.J., Moretti, J.E. et al. J Chem Crystallogr (2012) 42: 911. doi:10.1007/s10870-012-0334-5

Abstract

Amino alcohols are important ligands for the asymmetric catalytic hydroamination of aminoallenes to form chiral pyrrolidines. The amino alcohol d-N-cyclohexyl-diphenylvalinol was synthesized and crystallized by slow evaporation from a 7:1 ether:ethanol mixture. The molecule crystallizes in the monoclinic space group P21 with unit cell parameters a = 8.0724(8) Å, b = 14.4327(14) Å, c = 8.6752(9) Å and β = 107.098(2)° and contains one molecule in the asymmetric unit with all constituent atoms being on general positions. Close inspection of the solid-state structure revealed a strong intramolecular hydrogen bond between the hydrogen atom of the hydroxyl group and the amine nitrogen.

Graphical Abstract

Herein we report the solid state structure of the chiral amino alcohol D-N-cyclohexyl-diphenylvalinol, a molecule which can serve as a ligand for transition metal complexes that function as asymmetric hydroamination catalysts
https://static-content.springer.com/image/art%3A10.1007%2Fs10870-012-0334-5/MediaObjects/10870_2012_334_Figa_HTML.gif
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Keywords

HydroaminationAsymmetric catalysisChirality

Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Eric W. Reinheimer
    • 1
    • 4
  • A. J. Hickman
    • 2
  • J. E. Moretti
    • 2
  • X. Ouyang
    • 3
  • Katherine A. Kantardjieff
    • 1
    • 4
  • Adam R. Johnson
    • 2
  1. 1.Department of Chemistry, The W.M. Keck Foundation Center for Molecular StructureCalifornia State Polytechnic UniversityPomonaUSA
  2. 2.Department of ChemistryHarvey Mudd CollegeClaremontUSA
  3. 3.Department of Chemistry and Biochemistry, The W.M. Keck Foundation Center for Molecular StructureCalifornia State UniversityFullertonUSA
  4. 4.Department of Chemistry and Biochemistry, The W.M. Keck Foundation Center for Molecular StructureCalifornia State UniversitySan MarcosUSA