Asymmetric [4+2] cycloaddition of cyclopentadiene to N'-tosylimine of N-glyoxyloyl-(2R)-bornane-10,2-sultam

Article abstract of DOI:10.1016/S0957-4166(97)00305-4

The first synthesis of the N'-tosylimine of N-glyoxyloyl-(2R)-bomane-10,2-sultam using a modified Holmes method is described. The N'-tosylimine was used as a dienophile in the Lewis acid-catalyzed diastereoselective imino-Diels-Alder reaction with cyclopentadiene to give cycloadducts with good diastereoisomeric excess. The direction of the asymmetric induction depends on the Lewis acid used.