Enantioselective Preparation,Conformational Analysis and Absolute Configuration of Highly Substituted Aziridines |
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| Authors: | Giorgio Bencivenni Paolo Righi Lodovico Lunazzi Silvia Ranieri Michele Mancinelli Andrea Mazzanti |
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| Affiliation: | Department of Industrial Chemistry “Toso Montanari”, University of Bologna, Italy |
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| 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. Chirality 27:875–887, 2015. © 2015 Wiley Periodicals, Inc. |
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| Keywords: | aziridines organocatalysis dynamic‐NMR DFT calculations absolute configuration |
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