112344-91-9Relevant academic research and scientific papers
Synthesis of β-lactams by condensation of titanium enolates of 2-pyridylthioesters with imines. Influence of the imine structure on the trans/cis stereoselectivity
Annunziata, Rita,Benaglia, Maurizio,Cinquini, Mauro,Cozzi, Franco,Ponzini, Francesco,Raimondi, Laura
, p. 2939 - 2948 (2007/10/02)
The condensation of the titanium enolates of C-2 alkyl substituted 2-pyridylthioesters with imines affords β-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 β-lactams, while sterically non-requiring or chelating groups favour the formation of the cis-products. On the basis of NMR evidences a rationale is proposed to account for the observed stereoselectivity.
MILD AND CONVENIENT ONE-POT SYNTHESIS OF β-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES
Cinquini, Mauro,Cozzi, Franco,Cozzi, Pier Giorgio,Consolandi, Emanuela
, p. 8767 - 8774 (2007/10/02)
Treatment of 2-pyridylthioesters with triethylamine in the presence of titanium tetrachloride affords titanium enolates that add to imines to give β-lactams in fair to excellent yields with moderate to good stereoselectivity.
Preparation of 3-Alkyl β-Lactams via the Ketene-Imine Cycloaddition Reaction Using α-(Phenylthio)alkanoyl Halides as Starting Materials:Application to the Synthesis of (+/-)-Carbapenem Building Blocks and Related Compounds
Palomo, Claudio,Cossio, Fernando P.,Odiozola, Jose M.,Oiarbide, Mikel,Ontoria, Jesus M.
, p. 4418 - 4428 (2007/10/02)
Preparation of appropriately substituted 3-alkyl β-lactams via the ketene (or equivalent)-imine cycloaddition reaction is described.The dehydrochlorination reaction of α-(phenylthio)alkanoyl chlorides with triethylamine in the presence of imines derived f
The Reformatsky Type Reaction of Gilman and Speeter in the Preparation of Valuable β-Lactams in Carbapenem Synthesis: Scope and Synthetic Utility
Palomo, Claudio,Cossio, Fernando P.,Arrieta, Ana,Odriozola, Jose M.,Oiarbide, Mikel,Ontoria, Jesus M.
, p. 5736 - 5745 (2007/10/02)
The preparation of apppropriately substituted 3-alkyl β-lactams from the Reformatsky type reaction of Gilman and Speeter is described.Treatment of Schiff bases derived from α-methylcinnamaldehyde and amines with ethyl α-bromobutyrate or ethyl α-bromoisova
