Samarium Diiodide-Mediated Reductive Coupling of Epoxides and Carbonyl Compounds: A Stereocontrolled Synthesis of C-Glycosides from 1,2-Anhydro Sugars

Samarium Diiodide-Mediated Reductive Coupling of Epoxides and Carbonyl Compounds: A Stereocontrolled Synthesis of C-Glycosides from 1,2-Anhydro Sugars

Sugar mimics: 1,2‐anhydro sugars can be cross‐coupled with aldehydes and ketones under very mild conditions and using a wide range of protecting groups to give C‐glycosides in good yield in a radical reaction mediated by SmI2 (see scheme; A=no proton source, B=in the presence of water).

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Veröffentlicht in:Angewandte Chemie (International ed.) 2002-09, Vol.41 (17), p.3242-3246
Hauptverfasser: Chiara, Jose Luis, Sesmilo, Esther
Format: Artikel
Sprache:eng
Schlagworte:
C-glycosides
electron transfer
Epoxy Compounds - chemistry
Glycosides - chemical synthesis
Indicators and Reagents
Iodides - chemistry
Oxidation-Reduction
radical reactions
samarium
Samarium - chemistry
Stereoisomerism
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Zusammenfassung:Sugar mimics: 1,2‐anhydro sugars can be cross‐coupled with aldehydes and ketones under very mild conditions and using a wide range of protecting groups to give C‐glycosides in good yield in a radical reaction mediated by SmI2 (see scheme; A=no proton source, B=in the presence of water).
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20020902)41:17<3242::AID-ANIE3242>3.0.CO;2-I