Original Paper

Journal of Chemical Crystallography

, Volume 42, Issue 9, pp 911-915

First online:

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. ReinheimerAffiliated withDepartment of Chemistry, The W.M. Keck Foundation Center for Molecular Structure, California State Polytechnic UniversityDepartment of Chemistry and Biochemistry, The W.M. Keck Foundation Center for Molecular Structure, California State University
  • , A. J. HickmanAffiliated withDepartment of Chemistry, Harvey Mudd College
  • , J. E. MorettiAffiliated withDepartment of Chemistry, Harvey Mudd College
  • , X. OuyangAffiliated withDepartment of Chemistry and Biochemistry, The W.M. Keck Foundation Center for Molecular Structure, California State University
  • , Katherine A. KantardjieffAffiliated withDepartment of Chemistry, The W.M. Keck Foundation Center for Molecular Structure, California State Polytechnic UniversityDepartment of Chemistry and Biochemistry, The W.M. Keck Foundation Center for Molecular Structure, California State University Email author 
  • , Adam R. JohnsonAffiliated withDepartment of Chemistry, Harvey Mudd College Email author 

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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 P2 1 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

Hydroamination Asymmetric catalysis Chirality