Azide and Cyanide Displacements via Hypervalent Silicate Intermediates.
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.
Soli
Eric D.
ED
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323.
Manoso
Amy S.
AS
Patterson
Michael C.
MC
DeShong
Philip
P
Favor
David A.
DA
Hirschmann
Ralph
R
Smith
Amos B.
AB