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Updated: Sep 28, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Thermal/hyperbaric heterocycloaddition of 1,4-dialkoxy-1,3-dienes: the de novo (E,Z) way to sugars
Carole Bataille1, Gautier Bégin, Anne Guillam
1Laboratoire des Fonctions Azotées et Oxygénées Complexes, UMR 6014 CNRS, IRCOF, Université de Rouen, 76821-Mont St. Aignan Cedex, France.
Abstract:
1-(Z)-Alkoxy-4-(E)-methoxybutadiene derivatives have been reacted with ethylgyoxylate and diethyl ketomalonate under thermal or hyperbaric conditions. They provide, with a total regioselectivity and fair to total endoselectivities, the expected dihydropyranic cycloadducts. Three of those pseudo-glycals have been converted in a few classical steps (deprotection, reduction, and dihydroxylation) into (racemic) allose, mannose, and gullose derivatives. The order of these three steps has a direct influence on the efficiency of the transformation and determines the stereochemistry of the final sugar.
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