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. BELVISIPrimo
;C.M.A. GENNARISecondo
;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.
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