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Updated: Jan 5, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Photoredox-Catalyzed Stereoselective Radical Reactions to Synthesize Nucleoside Analogues with a C2'-Stereogenic
Fabiola Becerril-Jiménez1,2, Tommy Lussier1,2, Louis Leblanc1,2
1Bio-Organic Chemistry Laboratory , Institut de Recherches Cliniques de Montréal , Montréal , Québec H2W 1R7 , Canada.
Abstract:
The design of novel nucleoside analogues bearing a C2' all-carbon quaternary center is described. The construction of this all-carbon stereogenic center involves the use of photoredox catalysis to initiate an intramolecular attack of a silyl-tethered vinyl functionality on a tertiary radical. Density functional theory calculations were performed to explore the origin of the high syn diastereoselectivity obtained through the preferred 5-exo-trig cyclization mode. The intramolecular vinyl addition also enables the preparation of the complementary configuration of the C2' all-carbon stereocenter when performed after lactonization.
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