Sulfinyl-Mediated Stereoselective Functionalization of Acyclic Conjugated Dienes.
Ignacio ColomerMercedes UreñaAlma VisoRoberto Fernández de la PradillaPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2020)
The chemo- and stereocontrolled functionalization of conjugated sulfinyl dienes in a cascade process that involves a conjugate addition, diastereoselective protonation and a [2,3]-sigmatropic rearrangement is reported. Enantioenriched 1,4-diol and 1,4-aminoalcohol derivatives are obtained in a very straightforward manner. Further functionalization of these structures, including highly stereoselective epoxidation, dihydroxylation and the stereodivergent synthesis of several polyols in a controlled fashion is described.