DIASTEREOSELECTIVE INTRAMOLECULAR DIELS-ALDER REACTION OF THE FURAN DIENE, A FACILE ACCESS TO ENANTIOPURE EPOXY TETRAHYDROISOINDOLINES

Authors
ANDRES C MAESTRO G NIETO J PEDROSA R
Citation
C. Andres et al., DIASTEREOSELECTIVE INTRAMOLECULAR DIELS-ALDER REACTION OF THE FURAN DIENE, A FACILE ACCESS TO ENANTIOPURE EPOXY TETRAHYDROISOINDOLINES, Tetrahedron letters, 38(8), 1997, pp. 1463-1466
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
8
Year of publication
1997
Pages
1463 - 1466
Database
ISI
SICI code
0040-4039(1997)38:8<1463:DIDROT>2.0.ZU;2-R
Abstract
2-(2'-Furfuryl)-N-acryloyl tehahydro-1,3-benzoxazine 2a participates i n diastereoselective intramolecular Diels-Alder reaction in very mild conditions leading to two diastereoisomeric exo-adducts with good dias tereoselectivity. Chromatographic separation of both adduts, and furth er elimination of the menthol appendage allows to prepare enantiopure iso-indoline derivatives in excellent chemical yields. (C) 1997 Elsevi er Science Ltd.