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

Ernst Schaumann; Frank Tries

doi:10.1055/s-2002-19796

PAPER

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;

Abstract

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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.

Key words

dimethyldioxirane - silyl enol ethers - siloxyoxiranes - vinyloxiranes - epoxide ring opening

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