Asymmetric Diels-Alder Reactions of Chiral N-Methacryloylsultams with 1,3-Dienes

Article abstract of DOI:10.1016/S0040-4039(00)73222-9

R2AlCl-coordinated N-methacryloylsultam 1c undergoes efficient, endo-selective and highly diastereoface controlled <4+2>-additions to cyclopentadiene, isoprene, (E)-piperylene and the 2-silyloxydienes 10 and 12.The resulting cystalline cycloadducts are smoothly reduced with LiAlH4 providing the recovered auxiliary and the corresponding enentiomerically pure alcohols.