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. 2020 Apr 6;26(20):4620-4632.
doi: 10.1002/chem.201905742. Epub 2020 Mar 18.

Sulfinyl-Mediated Stereoselective Functionalization of Acyclic Conjugated Dienes

Ignacio Colomer  1 , Mercedes Ureña  1 , Alma Viso  1 , Roberto Fernández de la Pradilla  1
Affiliations

Sulfinyl-Mediated Stereoselective Functionalization of Acyclic Conjugated Dienes

Ignacio Colomer et al. Chemistry. .

Abstract

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.

Keywords: 1,4-aminoalcohols; 1,4-diols; [2,3]-sigmatropic rearrangement; sulfenate; sulfoxide.

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