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Title

Intramolecular Metal-free C(sp3)-H Activation Enables a Selective Mono O-Debenzylation of Fully Protected Aminosugars

AuthorsSantana, Andrés G. CSIC ORCID; Herrera, Antonio J. CSIC ; González Martín, Concepción C. CSIC ORCID
KeywordsO-Debenzylation
Intramolecular
Metal-free C(sp3)-H
Aminosugars
Issue DateNov-2021
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry (2021)
AbstractCarbamate-bearing benzylated aminosugars undergo an I2/I(III)-promoted intramolecular hydrogen atom transfer (IHAT) followed by a nucleophilic attack to provide polycyclic structures. Thus, suitably positioned benzyl ethers are surgically oxidized into the corresponding mixed N/O-benzylidene acetals, which can be conveniently deprotected under mild acidic conditions to grant access to selectively O-deprotected aminosugars amenable for further derivatization. The scope of this strategy has been proven with a battery of furanosic and pyranosic scaffolds. Preliminary mechanistic studies, including Hammett LFER and KIE analyses, support a reaction pathway with the nucleophilic cyclization as the rate-determining step.
Publisher version (URL)https://doi.org/10.1021/acs.joc.1c01977
URIhttp://hdl.handle.net/10261/254503
DOI10.1021/acs.joc.1c01977.
ISSN0022-3263
E-ISSN1520-6904
Appears in Collections:(IPNA) Artículos

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