A versatile and practical solvating agent for enantioselective recognition and NMR analysis of protected amines.
The 3,5-dinitrobenzoyl-derived 1-naphthylethyl amide 3 is an attractive CSA for NMR analysis of protected amines. It is readily prepared in a single step and combines practical resolution of diastereomeric complexes due to signal sharpness and effective signal separation. Crystallographic analysis shows that 3 forms a chiral cleft that can selectively bind one enantiomer of a substrate through hydrogen bonding, π-π stacking, and CH/π interactions. The enantioselective complex formation causes strong upfield shifts in the (1)H NMR spectrum even in the presence of only 5 mol % of 3.
Iwaniuk
Daniel P
DP
Department of Chemistry, Georgetown University, Washington, D C 20057, USA.
Wolf
Christian
C
D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D000588:Amines; D012997:Solvents