An Epoxide Ring-Opening Reaction via Hypervalent Silicate Intermediate: Synthesis of Statine

Hiroyuki Konno; Emi Toshiro; Naoyuki Hinoda

doi:10.1055/s-2003-41049

PAPER

An Epoxide Ring-Opening Reaction via Hypervalent Silicate Intermediate: Synthesis of Statine

Hiroyuki Konno*, Emi Toshiro, Naoyuki Hinoda
Department of Biological Science and Technology, Faculty of Engineering, University of Tokushima, 2-1 Minamijosanjima-cho, Tokushima, 770-8506, Japan
Fax: +81(88)6569213; e-Mail: konno@bio.tokushima-u.ac.jp;

Abstract

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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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