Lactol often exists as a mixture of two epimers in mono-, oligo-, and polysaccharides. Being able to convert the two epimers to one product in a dynamic kinetic diastereoselective process will offer efficient and stereoselective methods for carbohydrate synthesis. We recently developed several new catalytic reactions involving dynamic kinetic transformations of lactols. The first one is a iridium-catalyzed diastereoselective internal redox isomerization of Achmatowicz rearrangement product to carbohydrate lactones. The second one is a chiral organocatalyst mediated dynamic kinetic diastereoselective acylation of lactols derived from Achmatowicz rearrangement reaction[ii]. Both methods have been applied to de novo synthesis of mono- and oligosaccharides. The chiral catalyst-mediated acylation can also be extended to other hydroxyl groups in carbohydrates. H.-Y. Wang, K. Yang, S. R. Bennett, S.-R. Guo, W. Tang. Angew. Chem. Int. Ed. 2015, 54, 8756–8759. [ii] H.-Y. Wang, K. Yang, D. Yin, C. Liu, D. A. Glazier, W. Tang. “Chiral Catalyst-Directed Dynamic Kinetic Diastereoselective Acylation of Lactols for De Novo Synthesis of Carbohydrate”, Submitted.

Dynamic kinetic transformations of lactols for de novosynthesis of carbohydrate

251st National Meeting (2016)

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