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SYNTHESIS OF ENANTIOPURE SUBSTITUTED 1,4-DIOXANES BY MICHAEL INITIATED RING CLOSURE REACTIONS
Published: 01 November 2009 by MDPI in The 13th International Electronic Conference on Synthetic Organic Chemistry session 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.