119993-20-3Relevant academic research and scientific papers
Electroreductive intramolecular coupling of aromatic imino esters: Is four-membered cyclization much more favorable than six-membered cyclization?
Kise, Naoki,Hirano, Yuuki,Tanaka, Yoshi
, p. 1323 - 1325 (2006)
The electroreduction of an aromatic imino ester prepared from (S)-glutamic acid in the presence of chlorotrimethylsilane and triethylamine afforded a four-membered cyclized product, a mixed ketal of cis-2,4-disubstituted azetidine-3-one, stereospecificall
Synthesis and Penicillin-binding Protein Inhibitory Assessment of Dipeptidic 4-Phenyl-β-lactams from α-Amino Acid-derived Imines
Decuyper, Lena,Juki?, Marko,Sosi?, Izidor,Amoroso, Ana Maria,Verlaine, Olivier,Joris, Bernard,Gobec, Stanislav,D'hooghe, Matthias
, p. 51 - 55 (2020)
Monocyclic β-lactams revive the research field on antibiotics, which are threatened by the emergence of resistant bacteria. A six-step synthetic route was developed, providing easy access to new 3-amino-1-carboxymethyl-4-phenyl-β-lactams, of which the penicillin-binding protein (PBP) inhibitory potency was demonstrated biochemically.
Probing of the cis-5-phenyl proline scaffold as a platform for the synthesis of mechanism-based inhibitors of the Staphylococcus aureus sortase SrtA isoform
Kudryavtsev, Konstantin V.,Bentley, Matthew L.,McCafferty, Dewey G.
body text, p. 2886 - 2893 (2009/09/05)
cis-5-Phenyl prolinates with electrophilic substituents at the fourth position of a pyrrolidine ring were synthesized by 1,3-dipolar cycloaddition of arylimino esters with divinyl sulfone and acrylonitrile. 4-Vinylsulfonyl 5-phenyl prolinates inhibit Staphylococcus aureus sortase SrtA irreversibly by modification of the enzyme Cys184 and could be used as hits for the development of antibacterials and antivirulence agents.
Stereoselective synthesis of functional derivatives of 2-(2-carboxyethyl) pyrrolidine-2-carboxylic acid
Kudryavtsev,Nukolova,Kokoreva,Smolin
, p. 412 - 422 (2007/10/03)
Azomethine ylides generated from dimethyl 2-(arylmethylideneamino) pentanedioates by the action of AgOAc and Et3N reacted with dipolarophiles in regio- and stereoselective fashion to form 5-aryl-2-(2-carboxyethyl)pyrrolidine-2-carboxylic acid derivatives. 1,3-Dipolar cycloaddition of divinyl sulfone to the azomethine ylide generated from the Schiff base derived from methyl (S)-2-phthalimido-4-oxobutanoate and dimethyl glutamate gave chiral simplified kaitocephalin analogs. Pleiades Publishing, Inc., 2006.
X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES. PART 17. SEQUENTIAL MICHAEL ADDITION-5-ENDO-TRIG CYCLISATION OF ARYLIDENE IMINES OF Α-AMINO ACID ESTERS
Grigg, Ronald,Kemp, James,Malone, John F.,Rajviroongit, Shuleewan,Tangthongkum, Anant
, p. 5361 - 5374 (2007/10/02)
Imines of α-amino acid esters undergo regiospecific Michael addition to methyl acrylate or acrylonitrile in good yield in benzene at 25 degC catalysed by benzyltrimethylammonium methoxide (BTAM).The Michael adducts cyclise to a mixture of two stereoisomer
ALKYLATION OF SHIFF BASE ANIONS WITH ω-HALOGENO ESTERS: A LACTAM SYNTHESIS.
Mkhairi, A,Hamelin, J.
, p. 4435 - 4436 (2007/10/02)
Imine anions of α-aminoesters, obtained from NaH/DMSO are alkylated with ω-halogenoesters.Thermolysis of the alkylated compounds lead to functionnalized lactams.
5-Endo-Trig Cyclisation and 1,3-Anionic Cycloaddition in Arylimine Derivatives of α-Amino Acid Esters
Grigg, Ronald,Kemp, James,Malone, John,Tangthongkum, Anant
, p. 648 - 650 (2007/10/02)
Michael adducts of imines of α-amino acid esters are converted into a mixture of two stereoisomeric pyrrolidines by benzyltrimethylammonium methoxide (BTAM) apparently by a 5-endo-trig cyclisation.
