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A Versatile and Practical Solvating Agent for Enantioselective Recognition and NMR Analysis of Protected Amines

  作者 IWANIUK DANIEL P; WOLF CHRISTIAN  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-19;  页码  6724-6727  
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[摘要]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, pi-pi stacking, and CH/pi interactions. The enantioselective complex formation causes strong upfield shifts in the H-1 NMR spectrum even in the presence of only 5 mol % of 3.

 
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