The results obtained from a study on the stereochemical control in the dihydroxylation of the double bond of vinyl epoxides and their derivatives (bromo derivatives, azido derivatives and vinyl aziridines) are presented herein. A significant diastereoselectivity was observed for the bromo derivatives, azido derivatives and N-protected vinyl aziridines, whereas vinyl epoxides and unprotected vinyl aziridines showed no diastereoselectivity. The results obtained are generally consistent with the Kishi model. (C) 2012 Elsevier Ltd. All rights reserved.

Study on the stereochemical control of dihydroxylation of vinyl epoxides and their derivatives / Giuliana, Righi; Mandic', Emanuela; Naponiello, GAIA CLARA MERCEDES; Paolo, Bovicelli; Tirotta, Ilaria. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 68:14(2012), pp. 2984-2992. [10.1016/j.tet.2012.02.029]

Study on the stereochemical control of dihydroxylation of vinyl epoxides and their derivatives

MANDIC', EMANUELA;NAPONIELLO, GAIA CLARA MERCEDES;TIROTTA, ILARIA
2012

Abstract

The results obtained from a study on the stereochemical control in the dihydroxylation of the double bond of vinyl epoxides and their derivatives (bromo derivatives, azido derivatives and vinyl aziridines) are presented herein. A significant diastereoselectivity was observed for the bromo derivatives, azido derivatives and N-protected vinyl aziridines, whereas vinyl epoxides and unprotected vinyl aziridines showed no diastereoselectivity. The results obtained are generally consistent with the Kishi model. (C) 2012 Elsevier Ltd. All rights reserved.
2012
azidoalcohol; azidoalcohols; bromohydrins; dhydroxylation; dihydroxylation; vinyl aziridine; vinyl aziridines; vinyl epoxide; vinyl epoxides
01 Pubblicazione su rivista::01a Articolo in rivista
Study on the stereochemical control of dihydroxylation of vinyl epoxides and their derivatives / Giuliana, Righi; Mandic', Emanuela; Naponiello, GAIA CLARA MERCEDES; Paolo, Bovicelli; Tirotta, Ilaria. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 68:14(2012), pp. 2984-2992. [10.1016/j.tet.2012.02.029]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/512652
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