Azide and Cyanide Displacements via Hypervalent Silicate Intermediates
The Journal of Organic Chemistry1999Vol. 64(9), pp. 3171–3177
Citations Over TimeTop 10% of 1999 papers
Eric D. Soli, Amy S. Manoso, Michael C. Patterson, Philip DeShong, David A. Favor, Ralph Hirschmann, Amos B. Smith
Abstract
Hypervalent azido- and cyanosilicate derivatives, prepared in situ by the reaction of trimethylsilyl azide or trimethylsilyl cyanide, respectively, with tetrabutylammonium fluoride, are effective sources of nucleophilic azide or cyanide. Primary and secondary alkyl halides and sulfonates undergo rapid and efficient azide or cyanide displacement in the absence of phase transfer catalysts with the silicate derivatives. Application of these reagents to the stereoselective synthesis of glycosyl azide derivatives is reported.
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