Synthesis

Reactions of 2-Hydroxy-6, 8-dioxabicyclo [3.2. 1] oct-3-ene with Diethylaminosulfur Trifluoride and with Halogens. Facile Synthesis of 1, 6-Anhydrohalohexopyranoses

F Oberdorfer, R Haeckel, G Lauer

Index: Oberdorfer, Franz; Haeckel, Roland; Lauer, Gilbert Synthesis, 1998 , # 2 p. 201 - 206

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Citation Number: 8

Abstract

Abstract: D-Galactal 1 reacts in THF in the presence of catalytic amounts of concentrated sulfuric acid to give (2R)-2-hydroxy-6, 8-dioxabicyclo [3.2. 1] oct-3-ene (4) in a Ferrier-type rearrangement in 40% yield. When 4 is treated with diethylaminosulfur trifluoride (DAST) under certain reaction conditions, a novel intramolecular second order allylic rearrangement follows leading to previously unknown diastereomeric monofluoro derivatives 7 and 8. ...

~20%

~39%

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