The stereocontrolled formation of cyclic vicinal cis-diols via a samarium diiodide pinacol coupling of dialdehydes

4 páginas, 1 figura, 1 tabla.Aliphatic 1,5- and 1,6 dialdehydes with and without α-substituents, as well as derivatives of carbohydrate dialdehydes undergo a pinacol coupling reaction in the presence of SmI2 to give cis-diols as the preponderant products. When α-alkoxy groups are present, the diol has an orientation that is opposite to such groups. Aliphatic 1,5- and 1,6-dialdehydes with and without α-substituents as well as derivatives of carbohydrate dialdehydes undergo a pinacol coupling reaction in the presence of SmI2 to give cis-diols as the preponderant products. When α-alkoxy groups are present, the diol has an orientation that is opposite to such groups.We wish to thank NSERCC and FCAR for generous financial assistance. We also acknowledge a postdoctoral fellowship to J.L. C. from NATO and a sabbatical leave to W.C. from Farmitalia Carlo Erba.Peer reviewe