Electrochemical Synthesis of Imino‐ C ‐Nucleosides by “Reactivity Switching” Methodology for  in situ  Generated Glycoside Donors | Zendy

Okamoto Kazuhiro | Zendy; Tsutsui Mizuki | Zendy; Morizumi Haruka | Zendy; Kitano Yoshikazu | Zendy; Chiba Kazuhiro | Zendy

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Electrochemical Synthesis of Imino‐ C ‐Nucleosides by “Reactivity Switching” Methodology for in situ Generated Glycoside Donors

Author(s) -

Okamoto Kazuhiro,

Tsutsui Mizuki,

Morizumi Haruka,

Kitano Yoshikazu,

Chiba Kazuhiro

Publication year - 2021

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.202100106

Subject(s) - iminium , chemistry , reactivity (psychology) , regioselectivity , electrophile , electrochemistry , redox , combinatorial chemistry , in situ , anomer , stereochemistry , organic chemistry , ion , catalysis , electrode , medicine , alternative medicine , pathology

Redox‐induced regioselective C(sp 3 )‐H C ‐glycosidation for unactivated prolinols was achieved by controlling the anomeric reactivity of electrochemically generated iminium cations. A mechanistic study revealed that the intermediate was pooled as covalent azaribose or iminium cation species in situ , and the electrophilicity of intermediates can be adjusted by changing coexisting acids. We found that the armed/disarmed analogy concept of traditional glycochemistry can be adapted to our C ‐glycosidation reaction. Finally, we invented a logical synthetic methodology, named “reactivity switching” concept, and synthesized a series of imino‐ C ‐nucleosides ( C ‐azanucleosides) based on this methodology.

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