| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1383669 | Carbohydrate Research | 2014 | 5 Pages |
•C-Vinyl α-gluco, α-galacto, and β-mannopyranosides are selectively prepared.•Pd0-mediated cyclization affords C-vinyl glycosides by substrate control.•Double diastereoselection using DACH ligands amplifies the cyclization selectivity.•The C-vinyl pyranosides have a free C-2 OH for further elaboration.
Oct-2-enitols undergo a Pd0-mediated cyclization to produce C-vinyl α-gluco- and α-galactopyranosides, and C-vinyl β-mannopyranoside in good yield and with high stereoselectivity. While substrate control demonstrates a clear stereochemical preference during cyclization, the α- and β-epimeric ratios are enhanced by double diastereoselection using the (S,S) or (R,R)-DACH ligands.
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