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. - In: CHIRALITY. - ISSN 0899-0042. - STAMPA. - 27:12(2015), pp. 875-887. [10.1002/chir.22522]
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 spectraI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
