Enantiopure arenesulfenic acids as intermediates in stereoselective synthesis

Add time:08/06/2019    Source:sciencedirect.com

New transient arenesulfenic acids were involved in the synthesis of enantiopure 2-arylsulfinyl-1,3-dienes, showing central or axial chirality of the substituted arene residue, apart from the chirality related to the stereogenic sulfur atom. Some of the obtained dienes, that is, (Sa,SS)- and (SaRS)-2-(2′-hydroxy-1,1′-binaphthalen-2-sulfinyl)-3-methyl-1,3-butadienes, were subjected to diastereoselective Diels–Alder cycloadditions with N-methylmaleimide. Removal of the arylsulfoxide auxiliary, in the major adduct, was accomplished by reductive cleavage with Raney nickel.

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