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