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Paper | Special issue | Vol 93, No. 2, 2016, pp.723-736
Published online, 18th December, 2015
DOI: 10.3987/COM-15-S(T)64
Alkoxide-Directed Hydride Addition to α,β-Unsaturated Sultones

Kamal M. Dawood, Andrea Bramborg, Ahmed F. Darweesh, Katrin Spinde, Victor Rogachev, Anne Jäger, and Peter Metz*

*Organic Chemistry I, Department of Chemistry, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany

Abstract

Seven- and eight-membered β,γ-unsaturated sultones were readily prepared by ring closing metathesis. Epoxidation of these sultones and of an analogous six-membered sultone furnished the corresponding β,γ-epoxy sultones efficiently. Treatment of these epoxides with a suitable base gave α,β-unsaturated γ-hydroxy sultones in high yields. Reduction of both the α,β-unsaturated γ-hydroxy sultones and the epoxy sultones by Red-Al is likely to proceed in a hydroxyl-directed fashion via a mixed aluminate as the reactive intermediate.