Journal
CARBOHYDRATE RESEARCH
Volume 466, Issue -, Pages 30-38Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2018.02.010
Keywords
Cross coupling; Pd-catalysis; Anhydro-aldose tosylhydrazones; Carbenes; Substituted exo-glycals
Funding
- Hungarian Scientific Research Fund [OTKA K109450]
- Alexander von Humboldt Foundation
- EU
- European Regional Development Fund [GINOP-2.3.2-15-2016-00008]
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Palladium-catalyzed cross-couplings of O-peracylated and O-permethylated 2,6-anhydro-aldose tosylhydrazones with aryl halides were studied under thermic conditions in the presence of LiOtBu and phosphine ligands. The reactions gave the corresponding aryl substituted exo-glycals as mixtures of diastereomers in 11-75% yields. The transformations represent a new access to these types of glycomimetic compounds. The double bond of some aryl substituted exo-glycals was saturated to give good yields of benzylic C-glycosyl derivatives. (C) 2018 Elsevier Ltd. All rights reserved.
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