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.

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]

STEREOSELECTIVE RADICAL-MEDIATED CYCLIZATION OF NOREPHEDRINE DERIVED O-BROMOBENZAMIDES - ENANTIOSELECTIVE SYNTHESIS OF 4-SUBSTITUTED 1,2,3,4-TETRAHYDROISOQUINOLINES

L. BELVISI
Primo
;
C.M.A. GENNARI
Secondo
;
C. SCOLASTICO
Penultimo
;
1993

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.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/175960
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