SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES - INFLUENCE OF THE IMINE STRUCTURE ON THE TRANS/CIS STEREOSELECTIVITY
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ANNUNZIATA, R
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UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALYUNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
ANNUNZIATA, R
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BENAGLIA, M
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UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALYUNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
BENAGLIA, M
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CINQUINI, M
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UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALYUNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
CINQUINI, M
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COZZI, F
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UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALYUNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
COZZI, F
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PONZINI, F
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UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALYUNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
PONZINI, F
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RAIMONDI, L
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UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALYUNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
RAIMONDI, L
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[1] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
The condensation of the titanium enolates of C-2 alkyl substituted 2-pyridylthioesters with imines affords beta-lactams in trans/cis ratios that largely depend on the structure of the C-imine residue. Bulky and non-chelating heteroatom-containing groups lead to the formation of trans p-lactams, while sterically non-requiring or chelating groups favour the formation of the cia-products. On the basis of NMR evidences a rationale is proposed to account for the observed stereoselectivity.