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A Versatile and practical solvating agent for enantioselective recognition and NMR analysis of protected amines

Journal of Organic Chemistry, ISSN: 0022-3263, Vol: 75, Issue: 19, Page: 6724-6727
2010
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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 H NMR spectrum even in the presence of only 5 mol % of 3. © 2010 American Chemical Society.

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