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Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding
Jik Chin1, Dong Chan Kim, Hae-Jo Kim
1Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, Canada. jchin@chem.utoronto.ca
Organic Letters
|July 17, 2004
Abstract:
[structure: see text] A chiral aldehyde that forms resonance-assisted hydrogen bonded imines with amino acids has been developed. This hydrogen bond not only increases the equilibrium constant for imine formation but also provides a highly downfield-shifted NMR singlet for evaluating enantiomeric excess and absolute stereochemistry of amino acids.