ChemInform Abstract: Synthesis of Heterocyclic Systems with Carbohydrate Fragments. Part 1. Stereoselective Synthesis of Azoloanhydrosugars.

Abstract

Synthesis of Heterocyclic Systems with Carbohydrate Fragments. Part 1. Stereoselective Synthesis of Azoloanhydrosugars.-The base-catalyzed reaction of levoglucosenone (I) with various azoles is investigated. Whereas treatment of (I) with (II) in the presence of NEt3 leads stereoselectively to the Michael adducts (III), the reaction of (I) with, e.g. imidazole (IV), under piperidine catalysis gives a mixture of (V) and its gem. diol (VI). -(SAMET, A. V.; LAIKHTER, A. L.; REZNIKOV, D. N.; YAMSKOV, A. N.; UGRAK, B. I.; CHERNYSHEVA, N. B.; ELKIN, V. V.; SEMENOV, V. V.; Izv.