Crystal Structures of D-N-(2-Adamantyl)phenylglycinol and L-N-(2-Adamantyl)diphenylphenylalinol: Chiral Amino Alcohols Utilized as Ligands for Catalytic Asymmetric Hydroamination

Amino alcohols are important ligands for the asymmetric catalytic hydroamination of aminoallenes to form chiral pyrrolidines. Herein, we report the crystal structures of two chiral amino alcohols, D-N-(2-Adamantyl)phenylglycinol and L-N-(2-Adamantyl)diphenylphenylalinol, that function as ligands wit...

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Bibliographic Details
Published in:Molecular Crystals and Liquid Crystals Vol. 629; no. 1; pp. 70 - 77
Main Authors: Reinheimer, E. W., Kohn, A. W., Groeneman, R. H., Krueger, H. R., Kantardjieff, K., Johnson, A. R.
Format: Journal Article
Language:English
Published: Philadelphia Taylor & Francis 12.04.2016
Taylor & Francis Ltd
Subjects:
Alcohol
Alcohols
Asymmetry
Catalysis
Catalysts
chiral amino alcohol
Coordination compounds
Crystal structure
Diffraction
hydrogen bonding
Hydrogen bonds
Ligands
Molecular chemistry
Supramolecular chemistry
Transition metals
ISSN:1542-1406, 1563-5287, 1527-1943
Online Access:Get full text
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Summary:Amino alcohols are important ligands for the asymmetric catalytic hydroamination of aminoallenes to form chiral pyrrolidines. Herein, we report the crystal structures of two chiral amino alcohols, D-N-(2-Adamantyl)phenylglycinol and L-N-(2-Adamantyl)diphenylphenylalinol, that function as ligands within transition metal complexes that catalyze the hydroamination of aminoallenes. Both molecules crystallize in the noncentrosymmetric orthorhombic space group P2 1 2 1 2 1 . Inter- and intramolecular hydrogen bonding plays an important role in stabilizing each alcohol in the solid state in the absence of a transition metal. The presence of these hydrogen bonds has been verified by single crystal X-ray diffraction and their overall strength determined by computational methods.
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ISSN:1542-1406
1563-5287
1527-1943
DOI:10.1080/15421406.2015.1106907