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.

Facile conversion of sulfilimines into sulfoximines using dioxiranes

N. Gaggero
Primo
;
S. Colonna
Penultimo
;
1997

Abstract

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.
Dioxiranes; Oxidation; Sulfilimines; Sulfoximines
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/183835
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