Aryl(trifluoroethyl)iodonium Triflimide and Nitrile Solvent Systems: A Combination for the Stereoselective Synthesis of Armed 1,2-trans-β-Glycosides at Noncryogenic Temperatures
2015
Chu, An-Hsiang Adam | Minciunescu, Andrei | Bennett, Clay S.
Armed thioglycosides can be activated with aryl(trifluoroethyl)iodonium triflimide in 2:1 CH₂Cl₂/pivalonitrile or a solvent combination of CH₂Cl₂, acetonitrile, isobutyronitrile, and pivalonitrile (6:1:1:1) at 0 °C for glycosylation reactions that proceed in good yield and moderate to excellent selectivity (up to 25:1 β/α). Comparison to other common glycosylation promoters reveals that both the mixed solvent and the iodonium salt promoter are required for stereoselectivity.
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