Highly Stereoselective Synthesis of C-vinyl Pyranosides via a Pd0-mediated Cycloetherification of 1-acetoxy-2,3-dideoxy-oct-2-enithos
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.
Ezeh, Vivian C.; Nolen, Ernest G.; and Feeney, Matthew J., "Highly Stereoselective Synthesis of C-vinyl Pyranosides via a Pd0-mediated Cycloetherification of 1-acetoxy-2,3-dideoxy-oct-2-enithos" (2014). Carbohydrate Research 396. Faculty Publications. Paper 51.