Fluorine-directed 1,2-trans glycosylation of rare sugars
Nuria Aiguabella1, Mareike C Holland, Ryan Gilmour
1Institute for Organic Chemistry and Excellence Cluster EXC 1003 "Cells in Motion", Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany. ryan.gilmour@uni-muenster.de.
Abstract:
To reconcile the urgent need to access well defined β-configured 2,6-di-deoxypyranose analogues for chemical biology, with the intrinsic α-selectivity of the native system, the directing role of fluorine at C2 has been explored. Localised partial charge inversion (C-H(δ+)→ C-F(δ-)) elicits a reversal of the substrate-based α-stereoselectivity, irrespective of the protecting group electronics.
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