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Nickel-Mediated Synthesis of Non-Anomeric C-Acyl Glycosides through Electron Donor-Acceptor Complex Photoactivation.

ABSTRACT: The preparation of nonanomeric C-acyl-saccharides has been developed from two different carboxylic acid feedstocks. This transformation is driven by the synergistic interaction of an electron donor-acceptor complex and Ni catalysis. Primary-, secondary-, and tertiary redox-active esters are incorporated as coupling partners onto preactivated pyranosyl- and furanosyl acids, preserving their stereochemical integrity. The reaction occurs under mild conditions, without stoichiometric metal reductants or exogenous catalysts, using commercially available Hantzsch ester as the organic photoreductant.

SUBMITTER: Escolano M

PROVIDER: S-EPMC10412007 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Nickel-Mediated Synthesis of Non-Anomeric C-Acyl Glycosides through Electron Donor-Acceptor Complex Photoactivation.

Escolano Marcos M Cabrera-Afonso María Jesús MJ Ribagorda Maria M Badir Shorouk O SO Molander Gary A GA

The Journal of organic chemistry 20220315 7

The preparation of nonanomeric C-acyl-saccharides has been developed from two different carboxylic acid feedstocks. This transformation is driven by the synergistic interaction of an electron donor-acceptor complex and Ni catalysis. Primary-, secondary-, and tertiary redox-active esters are incorporated as coupling partners onto preactivated pyranosyl- and furanosyl acids, preserving their stereochemical integrity. The reaction occurs under mild conditions, without stoichiometric metal re ...[more]

PMID: 35289617

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