An Epoxide Ring-Opening Reaction via Hypervalent Silicate Intermediate: Synthesis of Statine
Hiroyuki Konno, Emi Toshiro, Naoyuki Hinoda · Synthesis · 2003
The azide- and cyanide-opening reaction of epoxide with TBAF and TMSN3 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.