Oxirane Ring Opening of Anhydrosugars with Alkynyl- and Alkenylaluminates

Abstract
The oxirane ring opening of 2,3-anhydro-pentopyranosides and 2,3-anhydro-hexopyranosides with organoaluminate reagents is described. By the use of trialkylalkynylaluminates, deoxy-alkynyl sugars are obtained in good yields. Trialkylalkenylaluminates are less efficient and react only with the pentosides. Vinylmagnesium bromide is used as an alternative reagent for the introduction of a vinyl group.

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