Journal
CHEMICAL SCIENCE
Volume 11, Issue 6, Pages 1531-1537Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc05173b
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Funding
- NSERC
- NSERC (Canada Research Chairs programs)
- McLean Foundation
- University of Toronto (McLean Award)
- Canada Foundation for Innovation [17545, 19119]
- Government of Ontario
- Kyoto University ICR-iJURC exchange program
- Sharcnet
- Compute Ontario
- Compute Canada
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In the presence of an arylboronic acid and a hydrogen atom transfer mediator under photoredox conditions, furanoside derivatives undergo site-selective redox isomerizations to 2-keto-3-deoxyfuranosides. Experimental evidence and computational modeling suggest that the transformation takes place by abstraction of the hydrogen atom from the 2-position of the furanoside-derived arylboronic ester, followed by C3-O bond cleavage via spin-center shift. This mechanism is reminiscent of the currently accepted pathway for the formation of 3 '-ketodeoxynucleotides by ribonucleotide reductase enzymes.
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