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Updated: Mar 30, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Enantioselective Preparation, Conformational Analysis and Absolute Configuration of Highly Substituted Aziridines
Giorgio Bencivenni1, Paolo Righi1, Lodovico Lunazzi1
1Department of Industrial Chemistry "Toso Montanari", University of Bologna, Italy.
Abstract:
The first example of organocatalytic aziridination reaction of α-substituted-α,β-unsaturated ketones is presented. The reaction was found to be highly enantio- and diastereoselective, yielding N-tosylated aziridines. Low-temperature nuclear magnetic resonance (NMR) spectra allowed for the determination of the N-inversion barrier, that was found to be quite lower with respect to unsubstituted aziridines. A thorough conformational analysis supported by low-temperature NMR data allowed for the determination of the absolute configuration of the main stereoisomer by means of time-dependent Density Functional Theory simulation of the electronic circular dichroism spectra.
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