Employing dimethyldioxirane, the direct conversion of several N-(p-tolylsulfonyl)sulfilimines and of one N-(acetyl)sulfilimine into the corresponding sulfoximines was achieved in high yield under mild conditions. Optically active S-(p-tolyl)-S-methyl-N-(p-tolylsulfonyl)sulfilimine could be transformed into its sulfoximine in high enantiomeric excess with retention of configuration. The effect of substituents indicates that the oxidation involves electrophilic O-transfer from the dioxirane to the sulfilimine sulfur.
Facile conversion of sulfilimines into sulfoximines using dioxiranes / N. Gaggero, L. D'Accolti, S. Colonna, R. Curci. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 38:31(1997), pp. 5559-5562.
Titolo: | Facile conversion of sulfilimines into sulfoximines using dioxiranes |
Autori: | GAGGERO, NICOLETTA (Primo) COLONNA, STEFANO (Penultimo) |
Parole Chiave: | Dioxiranes; Oxidation; Sulfilimines; Sulfoximines |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 1997 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/S0040-4039(97)01243-4 |
Appare nelle tipologie: | 01 - Articolo su periodico |