Tetrahedron

Reactivity of unsaturated sultones synthesized from unsaturated alcohols by ring-closing metathesis. Application to the racemic synthesis of the originally proposed …

A Le Flohic, C Meyer, J Cossy

Index: Le Flohic, Alexandre; Meyer, Christophe; Cossy, Janine Tetrahedron, 2006 , vol. 62, # 38 p. 9017 - 9037

Full Text: HTML

Citation Number: 26

Abstract

Unsaturated sultones have been synthesized from various primary or secondary alkenols by ring-closing metathesis of the corresponding unsaturated sulfonates. By treatment with a strong base, β, γ-unsaturated sultones can be metalated and subsequently alkylated with electrophiles. When iodomethylmagnesium chloride was selected as the electrophile, seven- membered ring β, γ-unsaturated sultones were converted into homoallylic conjugated (Z)- ...