Synthesis

An epoxide ring-opening reaction via hypervalent silicate intermediate: Synthesis of statine

H Konno, E Toshiro, N Hinoda

Index: Konno, Hiroyuki; Toshiro, Emi; Hinoda, Naoyuki Synthesis, 2003 , # 14 p. 2161 - 2164

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Citation Number: 19

Abstract

Abstract The azide-and cyanide-opening reaction of epoxide with TBAF and TMSN 3 in THF or TBAF and TMSCN in MeCN occurred regioselectively to afford β-hydroxy azides and cyanides in good yield. These hypervalent silicates have been shown to be highly effective as nucleophilic azide and cyanide donors under mild conditions. This methodology has been applied to the preparation of statine.