Open AccessAryl(trifluoroethyl)iodonium Triflimide and Nitrile Solvent Systems: A Combination for the Stereoselective Synthesis of Armed 1,2-trans-β-Glycosides at Noncryogenic Temperatures
Author(s) -
AnHsiang Adam Chu,
Andrei Minciunescu,
Clay S. Bennett
Publication year - 2015
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.5b03282
Subject(s) - chemistry , stereoselectivity , acetonitrile , solvent , aryl , glycosylation , nitrile , yield (engineering) , selectivity , glycoside , salt (chemistry) , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , alkyl , biochemistry , materials science , metallurgy
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.