Mixed‐Electrolyte‐Driven Stereoselective Electrochemical Glycosylation
Yuta IsodaDepartment of Chemistry and Biotechnology Graduate School of Engineering, Tottori University 4-101 Koyamachominami, Tottori city 680-8552 Tottori JapanKei KitamuraDepartment of Chemistry and Biotechnology Graduate School of Engineering, Tottori University 4-101 Koyamachominami, Tottori city 680-8552 Tottori JapanShuji TakahashiDepartment of Chemistry and Biotechnology Graduate School of Engineering, Tottori University 4-101 Koyamachominami, Tottori city 680-8552 Tottori JapanToshiki NokamiCenter for Research on Green Sustainable Chemistry Faculty of Engineering Tottori University 4-101 Koyamachominami, Tottori city 680-8552 Tottori JapanToshiyuki ItohCenter for Research on Green Sustainable Chemistry Faculty of Engineering Tottori University 4-101 Koyamachominami, Tottori city 680-8552 Tottori Japan
2019en
ABI
Abstract
Abstract Mixed electrolytes such as tetrabutylammonium triflate (Bu 4 NOTf) and tetrabutylammonium bis(trifluoromethanesulfonyl‐amide) (Bu 4 NNTf 2 ) were found to improve stereoselectivity in electrochemical glycosylation of thioglycosides building blocks without a stereocontrolling group. Bu 4 NOTf was crucial to generate glycosyl triflate intermediate, whereas a second electrolyte such as Bu 4 NNTf 2 contributes reducing solution resistance. Therefore, we assume that Bu 4 NOTf works as a reservoir of the triflate anion of the glycosyl triflate intermediate and Bu 4 NNTf 2 works only as an electrolyte.
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