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Synthesis 2003(14): 2161-2164
DOI: 10.1055/s-2003-41049
DOI: 10.1055/s-2003-41049
PAPER
© Georg Thieme Verlag Stuttgart · New York
An Epoxide Ring-Opening Reaction via Hypervalent Silicate Intermediate: Synthesis of Statine
Further Information
Received
16 May 2003
Publication Date:
22 August 2003 (online)
Publication History
Publication Date:
22 August 2003 (online)

Abstract
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.
Key words
hypervalent silicates - azido anion - cyano anion - amino acids - statine
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