Radical-mediated cyclization of norephedrine derived alpha-iodoamides 1 was found to be highly stereoselective (> 97.3) favouring diastereoisomer 2. Bicyclic lactams 2 were transformed in high yields into enantiomerically pure pyrrolidines 10. Transition state modelling with a force field developed ad hoc nicely predicts the stereochemical results.

STEREOSELECTIVE RADICAL-MEDIATED CYCLIZATION OF NOREPHEDRINE DERIVED ALPHA-IODOAMIDES - SYNTHESIS OF ENANTIOPURE PYRROLIDINES AND TRANSITION-STATE MODELING / L. BELVISI, C.M.A. GENNARI, G. POLI, C. SCOLASTICO, B. SALOM, M. VASSALLO. - In: TETRAHEDRON. - ISSN 0040-4020. - 48:19(1992), pp. 3945-3960.

STEREOSELECTIVE RADICAL-MEDIATED CYCLIZATION OF NOREPHEDRINE DERIVED ALPHA-IODOAMIDES - SYNTHESIS OF ENANTIOPURE PYRROLIDINES AND TRANSITION-STATE MODELING

L. BELVISI
Primo
;
C.M.A. GENNARI
Secondo
;
C. SCOLASTICO;
1992

Abstract

Radical-mediated cyclization of norephedrine derived alpha-iodoamides 1 was found to be highly stereoselective (> 97.3) favouring diastereoisomer 2. Bicyclic lactams 2 were transformed in high yields into enantiomerically pure pyrrolidines 10. Transition state modelling with a force field developed ad hoc 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/2434/176382
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