Diels-Alder Reactions of 1,2-(1,1'-Binaphthalene-2,2'-diyldisulfonyl)ethylene with Symmetrical and Unsymmetrical Dienes

Article abstract of DOI:10.1021/jo00005a041

The C2-symmetrical chiral reagent 1,2-(1,1'-binaphthalene-2,2'-diyldisulfonyl)ethylene (1) is a reactive dienopile and forms Diels-Alder adducts with symmetrical and unsymmetrical dienes.In the case of unsymmetrical dienes the reaction affords, in most cases, a single diastereomeric adduct whose stereochemistry has been determined by NMR spectroscopy and confirmed by X-ray structure determination of selected adducts.The arylsulfonyl groups can be removed with formation of a double bond, making 1 a chiral synthetic equivalent of acetylene in <4 + 2>-cycloaddition reactions.The binaphthyl auxiliary can be recovered and recycled.