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Total Stereoselective Michael Addition of N- and S- Nucleophiles to a D-Erythro...

Rocha, Juliana F.; Freitas, David S.; Noro, Jennifer Martins; Silva Teixeira, Carla S.; Sousa, Cristina E. A.; Alves, Maria José Chão

The synthesis of a 1,S-lactone 2,4-O-alkylidene-D-erythrose derivative was found to be a highly stereoselective template in Michael addition trough the reaction of a D-erythrosyl 1,5-lactone derivative with nitrogen and sulfur nucleophiles. The sulfur adducts formed are 1 (D-erythrose derivative):1 (nucleophile), and the nitrogen adducts are 1:2. Both were then treated under HCl to give 2,6-dideoxy-4-functional...


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