Sulfinyl-Mediated Stereoselective Functionalization of Acyclic Conjugated Dienes |
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| Authors: | Dr Ignacio Colomer Dr Mercedes Ureña Dr Alma Viso Prof Roberto Fernández de la Pradilla |
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| Institution: | Instituto de Química Orgánica General, IQOG-CSIC, Juan de la Cierva 3, 28006 Madrid, Spain |
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| 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. |
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| Keywords: | [2 3]-sigmatropic rearrangement 1 4-aminoalcohols 1 4-diols sulfenate sulfoxide |
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