The first example of organocatalytic aziridination reaction of α-substituted-α,β-unsaturated ketones was presented. The reaction was found to be highly enantio- and diastereoselective, yielding N-tosylated aziridines. Low temperature 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 TD-DFT simulation of the ECD spectra

Enantioselective Preparation, Conformational Analysis and Absolute Configuration of Highly Substituted Aziridines

BENCIVENNI, GIORGIO;RIGHI, PAOLO;LUNAZZI, LODOVICO;RANIERI, SILVIA;MANCINELLI, MICHELE;MAZZANTI, ANDREA
2015

Abstract

The first example of organocatalytic aziridination reaction of α-substituted-α,β-unsaturated ketones was presented. The reaction was found to be highly enantio- and diastereoselective, yielding N-tosylated aziridines. Low temperature 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 TD-DFT simulation of the ECD spectra
Bencivenni, Giorgio; Righi, Paolo; Lunazzi, Lodovico; Ranieri, Silvia; Mancinelli, Michele; Mazzanti, Andrea
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/525361
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