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Mixed‐Electrolyte‐Driven Stereoselective Electrochemical Glycosylation
Author(s) -
Isoda Yuta,
Kitamura Kei,
Takahashi Shuji,
Nokami Toshiki,
Itoh Toshiyuki
Publication year - 2019
Publication title -
chemelectrochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.182
H-Index - 59
ISSN - 2196-0216
DOI - 10.1002/celc.201900215
Subject(s) - trifluoromethanesulfonate , stereoselectivity , electrolyte , glycosyl , amide , electrochemistry , chemistry , glycosylation , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry , electrode
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.