Synthesis of Carbohydrate Derived α-Methylene-γ-lactones by Diasterecseldctive, Low Temperature Reformatsky-Type Reactions

René Csuk Institute of Organic Chemistry, Technical University Graz, A-8O10, Graz, Austria

Alois Fürstner Institute of Organic Chemistry, Technical University Graz, A-8O10, Graz, Austria

Heinz Sterk Institute of Organic Chemistry, Karl-Franzens-University, A-8010, Graz, Austria

Hans Weidmann Institute of Organic Chemistry, Technical University Graz, A-8O10, Graz, Austria

Abstract

Hexopyranoside- and hexofuranose uloses with either ethyl 2-(branamethyl)acrylate in the presence of laminar Zn/Ag-graphite or ethyl 2-(trimethylsilylinethyl)acrylate/tetra-n-butylanrnonium fluoride undergo stereoselective branching, mainly with formation of spiro α-methylene-γ-lactones.

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Synthesis of Carbohydrate Derived α-Methylene-γ-lactones by Diasterecseldctive, Low Temperature Reformatsky-Type Reactions

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Synthesis of Carbohydrate Derived α-Methylene-γ-lactones by Diasterecseldctive, Low Temperature Reformatsky-Type Reactions

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