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Usage Statistics Cite this paper as: Bagnoli, L.; Scarponi, C.; Testaferri, L.; Tiecco, M. SYNTHESIS OF ENANTIOPURE SUBSTITUTED 1,4-DIOXANES BY MICHAEL INITIATED RING CLOSURE REACTIONS. In Proceedings of the 13th Int. Electron. Conf. Synth. Org. Chem., 1-30 November 2009; Sciforum Electronic Conferences Series, 2009, d001:1-4.
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13th Int. Electron. Conf. Synth. Org. Chem. 2009, d001:1-4
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SYNTHESIS OF ENANTIOPURE SUBSTITUTED 1,4-DIOXANES BY MICHAEL INITIATED RING CLOSURE REACTIONS
Dipartimento di Chimica e Tecnologia del Farmaco Università di Perugia, Italy;
* Author to whom correspondence should be addressed.
(This article belongs to the section D. Symposium on Selenium and Tellurium Chemistry)
Abstract: Enantiomerically pure substituted 1,4-dioxanes have been prepared from vinyl phenyl selenones and the commercially available enantiopure 1,2-diols in the presence of sodium hydride. This simple and novel one step procedure is an example of the Michael initiated ring closure reactions (MIRC) and involves a conjugate addition of the alkoxide anions derived from the 1,2-diols to the vinyl phenyl selenones. The carbanions thus generated then suffer a proton transfer to give the alkoxide ions which effect the intramolecular displacement of the PhSeO2 group affording the substituted 1,4-dioxanes as the result of a ring closure reaction.
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