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

Authors

  • Eric W. Reinheimer
    • Department of Chemistry, The W.M. Keck Foundation Center for Molecular StructureCalifornia State Polytechnic University
    • Department of Chemistry and Biochemistry, The W.M. Keck Foundation Center for Molecular StructureCalifornia State University
  • A. J. Hickman
    • Department of ChemistryHarvey Mudd College
  • J. E. Moretti
    • Department of ChemistryHarvey Mudd College
  • X. Ouyang
    • Department of Chemistry and Biochemistry, The W.M. Keck Foundation Center for Molecular StructureCalifornia State University
    • Department of Chemistry, The W.M. Keck Foundation Center for Molecular StructureCalifornia State Polytechnic University
    • Department of Chemistry and Biochemistry, The W.M. Keck Foundation Center for Molecular StructureCalifornia State University
    • Department of ChemistryHarvey Mudd College
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
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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