Site-selective redox isomerizations of furanosides using a combined arylboronic acid/photoredox catalyst system

Author:

Dimakos Victoria1234,Gorelik Daniel1234,Su Hsin Y.1234,Garrett Graham E.1234ORCID,Hughes Gregory5678,Shibayama Hiromitsu1234,Taylor Mark S.1234ORCID

Affiliation:

1. Department of Chemistry

2. University of Toronto

3. Toronto

4. Canada

5. Global Process Chemistry

6. Merck Research Laboratories

7. Rahway

8. USA

Abstract

The combined action of boronic acid, photoredox catalyst and hydrogen atom transfer mediator enables the transformation of furanosides to 2-keto-3-deoxyfuranosides, a synthetic analog of the process catalyzed by the ribonucleotide reductase enzymes.

Funder

Compute Canada

Natural Sciences and Engineering Research Council of Canada

McLean Foundation

Canada Foundation for Innovation

Kyoto University

University of Toronto

Government of Ontario

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Reference50 articles.

1. Ribonucleotide reductases: radical enzymes with suicidal tendencies

2. Protein Radicals in Enzyme Catalysis

3. Chemical Synthesis of Nucleoside Analogues , ed. P. Merino , John Wiley & Sons , Hoboken, NJ , 2013

4. Some Aspects of Ribonucleoside Chemistry

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