Aryl(trifluoroethyl)iodonium Triflimide and Nitrile Solvent Systems: A Combination for the Stereoselective Synthesis of Armed 1,2-trans-beta-Glycosides at Noncryogenic Temperatures

作者：Adam An Hsiang; Minciunescu Andrei; Bennett Clay S

来源：Organic Letters, 2015, 17(24): 6262-6265.

DOI：10.1021/acs.orglett.5b03282

Armed thioglycosides can be activated With aryl(trifluoroethyl)iodonium triflimide in 2:1 CH2Cl2/pivalonitrle or a solvent combination of CH2Cl2, acetonitrile, isobutyronitrile, and pivalonitrile (6:1:1:1) at 0 degrees C for glycosylation reactions that proceed in good yield and:moderate to excellent selectivity (up to 25:1 beta/alpha). Comparison to other common glycosylation promoters reveals that :both the Mixed!, solvent and the iodonium salt promoter are required for stereoselectivity.

• 出版日期2015-12-18