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Updated: Jun 9, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
A versatile and practical solvating agent for enantioselective recognition and NMR analysis of protected amines
Daniel P Iwaniuk1, Christian Wolf
1Department of Chemistry, Georgetown University, Washington, D C 20057, USA.
Abstract:
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.
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