Azide and Cyanide Displacements via Hypervalent Silicate Intermediates

Autor: David A. Favor, Philip DeShong, Michael C. Patterson, Eric D. Soli, Ralph Hirschmann, Amy S. Manoso, Amos B. Smith
Rok vydání: 2001
Předmět:
Zdroj: The Journal of organic chemistry. 64(9)
ISSN: 1520-6904
Popis: 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.
Databáze: OpenAIRE