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

Article abstract of DOI:10.1016/S0040-4039(00)92024-0

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.