N-SUBSTITUTED HYDROXYSUCCINIMIDES FROM (S)-MALIC ACID AS NEW REAGENTS FOR ASYMMETRIC DIELS-ALDER ADDITION TO ENOATES

Article abstract of DOI:10.1016/S0040-4039(01)93808-0

(S)-N-Methyl-2-hydroxysuccinimide, easily available from natural (S)-malic acid, supplements the previously introduced (R)-pantolactone as chiral auxiliary for asymmetric Diels-Alder reactions of enoates, but yields products of opposite configuration.Practical large-scale preparations of enantiomer pairs of synthetically important Diels-Alder adducts, including adducts from crotonates, are described.