Azide and cyanide displacements via hypervalent silicate intermediates

被引:131
作者
Soli, ED
Manoso, AS
Patterson, MC
DeShong, P [1 ]
Favor, DA
Hirschmann, R
Smith, AB
机构
[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA
[2] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/jo982302d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:3171 / 3177
页数:7
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