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'Ring Opening–Ring Closure' Strategy for the Synthesis of Aryl-C-glycosides
- Source :
- The Journal of Organic Chemistry. 79:4676-4686
- Publication Year :
- 2014
- Publisher :
- American Chemical Society (ACS), 2014.
-
Abstract
- A new "ring-opening-ring closure" strategy for the synthesis of aryl-C-glycosides was described. This strategy exploited the nickel-catalyzed regioselective β-O elimination of glycals by reactions with various aryl boronic acids or potassium aryltrifluoroborates to yield the ring-opened products, which underwent the Lewis acid, protonic acid, PhSeCl, or NBS mediated ring closure reactions to afford diverse aryl-C-glycosides. After Lewis acids and protonic acids were screened, it was found that, starting from the ring-opened substrates, the Ph3PHBr or Sc(OTf)3 mediated ring closure reaction provided α- or β-preferred aryl-C-Δ(2,3)-glycosides, respectively. Furthermore, β-D-phenyl-C-glycosides were successfully prepared via the PhSeCl-mediated cyclization reaction, whereas the α-D-phenyl-C-glycoside was obtained via the NBS-mediated cyclization reaction. After removal of the 2-substituted functionalities by Bu3SnH/AIBN, the synthesis of 2-deoxy-aryl-C-glycosides was ultimately realized in a stereoselective manner.
- Subjects :
- Molecular Structure
Stereochemistry
Aryl
Potassium
Monosaccharides
Organic Chemistry
Closure (topology)
Regioselectivity
chemistry.chemical_element
Stereoisomerism
Ring (chemistry)
Medicinal chemistry
chemistry.chemical_compound
chemistry
Cyclization
Yield (chemistry)
Stereoselectivity
Glycosides
Lewis acids and bases
Lewis Acids
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 79
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....576ecde4706bad10cc496f06ed95422f