129101-41-3Relevant academic research and scientific papers
Asymmetric syntheses of 1-amino-2-phenyl(alkyl)cyclopropanecarboxylic acids by diastereoselective cyclopropanation of highly functionalized monochiral olefines
Alcaraz,Alcaraz, Carmen,Fernandez,Fernaendez, Ma. Dolores,De Frutos,De Frutos, Ma. Pilar,Marco,Marco, Josee L.,Bernabe,Bernabe, Manuel,Foces-Foces,Foces-Foces, Concepcion,Cano,Cano, Felix H.
, p. 12443 - 12456 (2007/10/02)
Monochiral α-benzamidocinnamic esters of N-methylephedrine or mandelic derivatives and benzylidene or alkylidene diketopiperazines, all obtained from oxazolones, react with diazomethane to give moderate to high diastereomeric excesses (d.e.) of pyrazoline
New α,β-Didehydroamino Acid Derivatives as Precursors in the Synthesis of 1-Aminocyclopropanecarboxylic Acids
Cativiela, Carlos,Diaz-de-Villegas, Maria D.,Jimenez, Ana I.
, p. 9157 - 9166 (2007/10/02)
The reaction of N-(diphenylmethylene)didehydroalanine methyl ester and N-didehydroalanine methyl ester with diazoalkanes or ylides gives the corresponding cyclopropane derivatives in high yields.The cis/trans ratio of these compounds was dependent on substrate, reagent and reaction temperature.From stereochemically homogeneous compounds the corresponding 1-aminocyclopropanecarboxylic acids were easily obtained by acid hydrolysis.
1-Aminocyclopropane-1-carboxylic acid derivatives: A new, general synthesis and NMDA receptor complex binding affinity study
Spadoni,Balsamini,Bedini,Mugnaini
, p. 1663 - 1674 (2007/10/02)
A new synthesis of 1-aminocyclopropane-1-carboxylic acid and of its (E)- and (Z)-2-substituted analogues (R = CH3;i-Pr;C6H5) has been performed by means of the 'diazo-addition' method, starting from N-(diphenylmethylene)-2,3-dehydro-1-amino-1-carboxylate precursors. The (E)- and (Z)-2-phenyl and the (Z)-2-methylcyclopropaneamino acids have been obtained with high diastereospecificity. All the cyclopropaneamino acids prepared were tested for their affinity for some glutamate receptors and resulted inactive, wich the exception of compounds (E)-1b and (Z)-1c which showed a shallow displacement of [H]-glycine binding.
SYNTHESIS OF ASYMMETRIC 1-AMINO-2-PHENYLCYCLOPROPANECARBOXYLIC ACIDS BY DIASTEREOSELECTIVE CYCLOPROPANATION OF HIGHLY FUNCTIONALIZED HOMOCHIRAL OLEFINES
a Pilar de,Marco, Jose L.,Fernandez-Alvarez, Eldiberto,Bernabe, Manuel
, p. 3101 - 3104 (2007/10/02)
Homochiral benzylidenediketopiperazine and α-benzoylaminocinnamic esters react with diazomethane giving high to good diastereomeric ratios of spiropyrazoline derivatives which, on photolysis and acid hydrolysis of the resulting spirocyclopropyl compounds
Reaction of 4-Methylene-5(4H)-oxazolones With Diazomethane
Arenal, I.,Bernabe, M.,Alvarez, E. Fernandez,Izquierdo, M. L.,Penades, S.
, p. 607 - 614 (2007/10/02)
The reaction of diazomethane with some (E) and (Z)-2-substituted-4-methylene-5(4)-oxazolones (1a-c) under two different conditions, has been studied. (E) and (Z)-1,2-disubstituted-7-oxo-6-oxa-4-azaspiro-hept-4-enes (3a-c, 4a-c) were mainly obtained, together with multiple addition compounds.The reaction showed to be stereoselective only when the substituents were aromatic.Acid hydrolysis of compounds 3a and 4a produced a mixture of (E) and (Z)-3,5-disubstituted-tetrahydrofuran-2-ones (8a, 9a).Smooth methanolysis of the ring led to (E) and (Z)-1-benzamido-cyclopropanecarboxylic esters (10a-c, 11a-c), which, on acid hydrolysis, gave (E) and (Z)-1-amino-2-phenylcyclopropanecarboxylic acids 12a and 13a.The pmr spectra have been analyzed by an iterative computer method, and the computed best values obtained have been used to deduce the stereochemistry of the spiroderivatives.
