Iron-catalyzed iodonium ion promoted activation of conventional thioglycosides for stereoselective 1,2-<i>cis</i> furanosylations

Iron-catalyzed activation of conventional thioglycosides using the iodonium ion enabled the selective synthesis of 1,2-<i>cis</i> furanosides. This strategy accommodates diverse furanosyl donors (D-ribose, D-arabinose, L-arabinose) and various <i>O</i>-nucleophiles (1°, 2°, 3°). Additionally, 1,2-<i>cis</i> hexaribofuranoside was synthesized, and the influence of the C2 functional group on selectivity was investigated.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc01597a
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
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article

Iron-catalyzed iodonium ion promoted activation of conventional thioglycosides for stereoselective 1,2-cis furanosylations

Indrajeet Sharma, Umesh Chaudhary, Sundaram Singh, Adrienne Daróczi
Chemical Communications
Carbohydrate Chemistry and Synthesis
article

Iron-catalyzed iodonium ion promoted activation of conventional thioglycosides for stereoselective 1,2-cis furanosylations

Indrajeet Sharma, Umesh Chaudhary, Sundaram Singh, Adrienne Daróczi
article en

Abstract

Iron-catalyzed activation of conventional thioglycosides using the iodonium ion enabled the selective synthesis of 1,2-<i>cis</i> furanosides. This strategy accommodates diverse furanosyl donors (D-ribose, D-arabinose, L-arabinose) and various <i>O</i>-nucleophiles (1°, 2°, 3°). Additionally, 1,2-<i>cis</i> hexaribofuranoside was synthesized, and the influence of the C2 functional group on selectivity was investigated.

Chemical CommunicationsVol. 61(53)
University of Oklahoma (US)
Openalex Percentile: Top 91%
Carbohydrate Chemistry and Synthesis
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