The reaction of the titanium enolalc of a 2-pyridylthioesler derived from (R)-3-hydroxybutync acid with chiral imines affords 3,3′-anti-3,4-trans configurated β-lactams in a highly selective fashion. The methodology has been applied to the synthesis of a precursor of the carbapenem antibiotic 1β-methylthienamycin.
HIGHLY STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF THE TITANIUM ENOLATE OF A CHIRAL 2-PYRIDYLTHIOESTER WITH CHIRAL IMINES / R. Annunziata, M. Benaglia, A. Chiovato, M. Cinquini, F. Cozzi. - In: TETRAHEDRON. - ISSN 0040-4020. - 51:36(1995), pp. 10025-10032.
HIGHLY STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF THE TITANIUM ENOLATE OF A CHIRAL 2-PYRIDYLTHIOESTER WITH CHIRAL IMINES
R. AnnunziataPrimo
;M. BenagliaSecondo
;M. CinquiniPenultimo
;F. CozziUltimo
1995
Abstract
The reaction of the titanium enolalc of a 2-pyridylthioesler derived from (R)-3-hydroxybutync acid with chiral imines affords 3,3′-anti-3,4-trans configurated β-lactams in a highly selective fashion. The methodology has been applied to the synthesis of a precursor of the carbapenem antibiotic 1β-methylthienamycin.
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