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

Righi, Giuliana and Mandic, Emanuela and Naponiello, Gaia Clara Mercedes and Bovicelli, Paolo and Tirotta, Ilaria (2012) Study on the stereochemical control of dihydroxylation of vinyl epoxides and their derivatives. Tetrahedron, Vol. 68 (14), p. 2984-2992. eISSN 1464-5416. Article.

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DOI: 10.1016/j.tet.2012.02.029

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.

Item Type:Article
ID Code:8732
Status:Published
Refereed:Yes
Uncontrolled Keywords:Dihydroxylation, vinyl epoxides, vinyl aziridines, azidoalcohols, bromohydrins
Subjects:Area 05 - Scienze biologiche > BIO/10 Biochimica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Elsevier Science
eISSN:1464-5416
Deposited On:04 Mar 2013 10:09

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