517913-98-3Relevant academic research and scientific papers
Stereoselective synthesis of all stereoisomers of orthogonally protected cyclobutane-1,2-diamine and some chemoselective transformations
Sans, Marta,Illa, Ona,Ortuno, Rosa M.
, p. 2431 - 2433 (2012/07/13)
The four stereoisomers of protected cyclobutane-1,2-diamine have been prepared in an enantio- and diastereocontrolled manner through stereodivergent synthetic routes starting from a half-ester as a common chiral precursor. Orthogonal protection allows the
(+)- and (-)-2-aminocyclobutane-1-carboxylic acids and their incorporation into highly rigid β-peptides: Stereoselective synthesis and a structural study
Izquierdo, Sandra,Rua, Federico,Sbai, Abdelouahid,Parella, Teodor,Alvarez-Larena, Angel,Branchadell, Vicenc,Ortuno, Rosa M.
, p. 7963 - 7971 (2007/10/03)
Several derivatives of (+)- and (-)-2-aminocyclobutane-1-carboxylic acid, 1, have been prepared through enantiodivergent synthetic sequences. The stereoselective synthesis of free amino acid (+)-1 has been achieved, and this product has been fully charact
Stereodivergent syntheses of the first bis(cyclobutane) β-dipeptides
Izquierdo, Sandra,Martin-Vila, Marta,Moglioni, Albertina G.,Branchadell, Vicenc,Ortuo, Rosa M.
, p. 2403 - 2405 (2007/10/03)
The efficient synthesis of methyl 2-benzyloxycarbonylamino-(1S,2R)-cyclobutane-1-carboxylate starting from 2-methoxycarbonyl-(1R,2S)-cyclobutane-1-carboxylic acid is described. This β-amino acid derivative is antipodal with respect to the (1R,2S)-compound
Enantioselective synthetic approaches to cyclopropane and cyclobutane β-amino acids: Synthesis and structural study of a conformationally constrained β-dipeptide
Martin-Vila, Marta,Muray, Elena,Aguado, Gemma P.,Alvarez-Larena, Angel,Branchadell, Vicenc,Minguillon, Cristina,Giralt, Ernest,Ortuo, Rosa M.
, p. 3569 - 3584 (2007/10/03)
Synthetic approaches to carbocyclic compounds, namely cyclopropane and cyclobutane β-amino acids, are presented. One of them is based on enzymatic desymmetrization of meso diesters, leading to the enantioselective production of cis-hemiesters, which afforded β-amino acids through Curtius rearrangements. The enantiomeric excess for the cyclobutane derivatives was 91% whereas the cyclopropanes were obtained in 63% ee. According to another strategy, an enantiomerically pure cyclopropane trans-β-amino acid, bearing a quaternary center, has been synthesized from a homochiral precursor easily available from D-glyceraldehyde. The preparation and structural investigation of the first synthesized cyclobutane containing dipeptide is also described. A hairpin-like conformation of this molecule in the solid state has been demonstrated by X-ray structural analysis, showing crystal packing induced by the presence of the rigid cyclobutane moiety and the formation of intermolecular hydrogen bonds. NMR experiments confirmed that these molecules also tend to produce aggregates in solution. On the contrary, theoretical calculations suggest that intramolecular interactions are important in the gas phase, as expected. Copyright (C) 2000 Elsevier Science Ltd.
Stereoselective synthesis of (-)-(1R,2S)-2-aminocyclobutane-1-carboxylic acid, a conformationally constrained β-amino acid
Martin-Vila, Marta,Minguillon, Cristina,Ortuno, Rosa M.
, p. 4291 - 4294 (2007/10/03)
The title compound as well as some derivatives have been synthesized for the first time in optically active form by means of a chemoenzymatic transformation used to induce asymmetry in achiral precursors. The enantio- and diastereomeric purity has been determined by HPLC and NMR techniques.
