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.
Titolo: | OPTICALLY-ACTIVE AMINOALCOHOL PROMOTED ADDITION OF 2-PYRIDYLTHIOESTER BORON ENOLATES TO IMINES - ENANTIOSELECTIVE ONE-POT SYNTHESIS OF BETA-LACTAMS |
Autori: | ANNUNZIATA, RITA MARIA (Primo) BENAGLIA, MAURIZIO (Secondo) RAIMONDI, LAURA MARIA (Ultimo) |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 1995 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/0040-4020(95)00503-Z |
Appare nelle tipologie: | 01 - Articolo su periodico |