Synthesis 2002(2): 0191-0194
DOI: 10.1055/s-2002-19796
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New General Route to Acceptor-Substituted Vinyloxiranes via Siloxyoxiranes - Novel Promising Synthetic Building-Blocks

Ernst Schaumann*, Frank Tries
Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstraße 6, 38678 Clausthal-Zellerfeld, Germany
Fax: +49(5323)722858; e-Mail: ernst.schaumann@tu-clausthal.de;
Weitere Informationen

Publikationsverlauf

Received 16 August 2001
Publikationsdatum:
03. August 2004 (online)

Abstract

Epoxidation of silyl enol ethers 2a,b with dimethyldioxirane yields siloxyoxiranes 3a,b. Anions 4a-d lead to nucleophilic ring-opening in the acetal position C-1 of 3 to give diols 5a-d. Monotosylation and cyclisation provide acceptor-substituted vinyloxiranes 6a-d.