The enolates derived from 2-pyridylthioesters by treatment with BCl3 . Me(2)S and enantiomerically pure aminoalcohols react with aromatic and heteroaromatic imines to afford beta-lactams in a convenient one-pot procedure and in up to 78% e.e. The aminoalcohol can be employed both as the metal ligand and as the base to generate the enolate. Among several aminoalcohols tested, N-methylephedrine turned our to be the more efficient in terms of stereoselectivity.
OPTICALLY-ACTIVE AMINOALCOHOL PROMOTED ADDITION OF 2-PYRIDYLTHIOESTER BORON ENOLATES TO IMINES - ENANTIOSELECTIVE ONE-POT SYNTHESIS OF BETA-LACTAMS / R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, V. Molteni, L. Raimondi. - In: TETRAHEDRON. - ISSN 0040-4020. - 51:32(1995), pp. 8941-8952. [10.1016/0040-4020(95)00503-Z]
OPTICALLY-ACTIVE AMINOALCOHOL PROMOTED ADDITION OF 2-PYRIDYLTHIOESTER BORON ENOLATES TO IMINES - ENANTIOSELECTIVE ONE-POT SYNTHESIS OF BETA-LACTAMS
R. AnnunziataPrimo
;M. BenagliaSecondo
;M. Cinquini;F. Cozzi;L. RaimondiUltimo
1995
Abstract
The enolates derived from 2-pyridylthioesters by treatment with BCl3 . Me(2)S and enantiomerically pure aminoalcohols react with aromatic and heteroaromatic imines to afford beta-lactams in a convenient one-pot procedure and in up to 78% e.e. The aminoalcohol can be employed both as the metal ligand and as the base to generate the enolate. Among several aminoalcohols tested, N-methylephedrine turned our to be the more efficient in terms of stereoselectivity.
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