Events The 13th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session d. Symposium on Selenium and Tellurium Chemistry of the event The 13th International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 2009

Citation

Marcello Tiecco, Lorenzo Testaferri, Catalina Scarponi, Luana Bagnoli, SYNTHESIS OF ENANTIOPURE SUBSTITUTED 1,4-DIOXANES BY MICHAEL INITIATED RING CLOSURE REACTIONS, in Proceedings of The 13th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2009, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-13-00226

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SYNTHESIS OF ENANTIOPURE SUBSTITUTED 1,4-DIOXANES BY MICHAEL INITIATED RING CLOSURE REACTIONS

Marcello Tiecco ¹

Lorenzo Testaferri ¹

Catalina Scarponi ¹

Luana Bagnoli ¹

1. Dipartimento di Chimica e Tecnologia del Farmaco Università di Perugia, Italy

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.

Keywords

Design and Synthesis of substituted oxazolones and their antibacterial activity

Selenium catalyzed oxidation of alkynes in aqueous media