STEREOSELECTIVE RADICAL-MEDIATED CYCLIZATION OF NOREPHEDRINE DERIVED O-BROMOBENZAMIDES - ENANTIOSELECTIVE SYNTHESIS OF 4-SUBSTITUTED 1,2,3,4-TETRAHYDROISOQUINOLINES
Articolo
Data di Pubblicazione:
1993
Citazione:
STEREOSELECTIVE RADICAL-MEDIATED CYCLIZATION OF NOREPHEDRINE DERIVED O-BROMOBENZAMIDES - ENANTIOSELECTIVE SYNTHESIS OF 4-SUBSTITUTED 1,2,3,4-TETRAHYDROISOQUINOLINES / L. BELVISI, C.M.A. GENNARI, G. POLI, C. SCOLASTICO, B. SALOM. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 4:2(1993), pp. 273-280. [10.1016/S0957-4166(00)82347-2]
Abstract:
Radical-mediated cyclization of norephedrine derived o-bromobenzamide 5 was found to be fairly stereoselective (85:15)favouring diastereoisomer trans-6. Tricyclic delta-lactams 6 were transformed in high yield into enantiomerically enriched (R)-1,2,3,4-tetrahydro-2,4-dimethylisoquinoline 8. Transition state modelling with a force field developed ad hoc (see also: Belvisi, L. et al. Tetrahedron 1992, 48, 3945) nicely predicts the stereochemical results.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
L. BELVISI, C.M.A. GENNARI, G. POLI, C. SCOLASTICO, B. SALOM
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