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

✍ Scribed by Celia Andrés; Gregorio Maestro; Javier Nieto; Rafael Pedrosa; Santiago García-Granda; Enrique Pérez-Carreño

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
190 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

2-(2'-Furfuryl)-N-aczyloyl tetrahydm-1 ~-henzoxaz~ 2a participates in diastercoselective intramolecular Diels-Alder reaction in very mild conditions leading to two diasterecisemeric exo-adduets with good diastereoseleclivity.

Chromatographic sel~ration of both adduts, and further elimination of the menthol appendage allows to Pretmre enantiopure iso-indo~ne derivatives in excellent chemical yields.

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