“Ring Opening–Ring Closure” Strategy for the Synthesis of Aryl-C-glycosides
Citations Over TimeTop 16% of 2014 papers
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.
Related Papers
- → Recent Advances in the Regioselective Synthesis of Pyrazoles(2011)73 cited
- → Perfectly Regioselective and Sequential Protection of Glucopyranosides(2010)53 cited
- → Remote substituent effects on regioselectivity in the Pauson–Khand reaction of 2-substituted norbornenes(2001)19 cited
- → Highly chemo/regioselective alkoxycarbonylation of terminal allenes catalyzed by Ru/N-ligand system(2023)3 cited
- → β-Aminoenones in the regioselective synthesis of 1,3,5-trialkylpyrazoles. The influence of the substituents in the mechanism and the regioselectivity of the reaction(1998)12 cited