Diastereoselective intramolecular Diels-Alder reaction of the furan diene. A facile access to enantiopure epoxy tetrahydroisoindolines

Article abstract of DOI:10.1016/S0040-4039(97)00058-0

2-(2'-Furfuryl)-N-acryloyl tetrahydro-1,3-benzoxazine 2a participates in diastereoselective intramolecular Diels-Alder reaction in very mild conditions leading to two diastereoisomeric exo-adducts with good diastereoselectivity. Chromatographic separation of both adduts, and further elimination of the menthol appendage allows to prepare enantiopure iso-indoline derivatives in excellent chemical yields.