Substrate-Controlled Direct α‑Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C6F5)3 as Catalyst

B­(C6F5)3 enables the metal-free unprecedented substrate-controlled direct α-stereoselective synthesis of deoxyglycosides from glycals. 2,3-Unsaturated α-O-glycoside products are obtained with deactivated glycals at 75 °C in the presence of the catalyst, while 2-deoxyglycosides are formed using acti...

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Published inJournal of organic chemistry Vol. 84; no. 5; pp. 2415 - 2424
Main Authors Sau, Abhijit, Palo-Nieto, Carlos, Galan, M. Carmen
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 01.03.2019
Subjects
Boranes - chemistry
Catalysis
Ethers, Cyclic - chemistry
Glycosides - chemical synthesis
Glycosylation
Hydrocarbons, Fluorinated - chemistry
Stereoisomerism
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Summary:B­(C6F5)3 enables the metal-free unprecedented substrate-controlled direct α-stereoselective synthesis of deoxyglycosides from glycals. 2,3-Unsaturated α-O-glycoside products are obtained with deactivated glycals at 75 °C in the presence of the catalyst, while 2-deoxyglycosides are formed using activated glycals that bear no leaving group at C-3 at lower temperatures. The reaction proceeds in good to excellent yields via concomitant borane activation of glycal donor and nucleophile acceptor. The method is exemplified with the synthesis of a series of rare and biologically relevant glycoside analogues.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.8b02613