156358-31-5Relevant academic research and scientific papers
Chiral phenylselenyl derivatives of pyrrolidine and Cinchona alkaloids: nitrogen-selenium donating ligands in palladium-catalyzed asymmetric allylic alkylation
Zielinska-Blajet, Mariola,Siedlecka, Renata,Skarzewski, Jacek
, p. 131 - 136 (2007)
Enantiomeric pyrrolidine alcohols and Cinchona alkaloids reacted with PhSeCN/Bu3P in toluene at 0-25 °C to give the corresponding phenyl selenides with complete inversion of configuration at the substitution centers. Thus, the chiral selenoethe
Mild and selective silicon-mediated access to enantioenriched 1,2-mercaptoamines and β-amino arylchalcogenides
Tanini, Damiano,Borgogni, Cosimo,Capperucci, Antonella
supporting information, p. 6388 - 6393 (2019/04/25)
Metal-free ring opening reactions of activated and unactivated aziridines with different silyl chalcogenides are described. Judicious tuning of the reaction conditions enables the synthesis of chiral enantioenriched N-Ts and N-Boc 1,2-mercaptoamines in good yields from the corresponding aziridines and bis(trimethylsilyl)sulfide. N-Protected and N-H unactivated aziridines are efficiently converted into the corresponding β-arylchalcogeno amines upon treatment with suitable arylchalcogenosilanes. The silicon-mediated ring opening reactions proceed with excellent regioselectivity and stereospecificity, allowing to access a wide array of synthetically and biologically valuable enantioenriched chalcogenoamines.
Sulfur, selenium and tellurium containing amines act as effective carbonic anhydrase activators
Tanini, Damiano,Capperucci, Antonella,Supuran, Claudiu T.,Angeli, Andrea
, p. 516 - 522 (2019/03/29)
A new series of β-aminochalcogenides were designed and synthesized to identify new carbonic anhydrase activator (CAA) agents as novel tools for the management of several neurodegenerative and metabolic disorders which represent a clinical challenge withou
Efficient ring opening of protected and unprotected aziridines promoted by stable zinc selenolate in ionic liquid
Salman, Syed M.,Schwab, Ricardo S.,Alberto, Eduardo E.,Vargas, Josimar,Dornelles, Luciano,Rodrigues, Oscar E. D.,Braga, Antonio L.
supporting information; experimental part, p. 69 - 72 (2011/02/25)
A highly efficient protocol is reported for the synthesis of chiral β-seleno amines via the ring-opening reaction of aziridines. Under neutral conditions, employing a stable phenyl selenolate specie (PhSeZnBr) and (BMIM)BF4 as solvent, β-seleno
Ring opening of unprotected aziridines by zinc selenolates in a biphasic system
Braga, Antonio L.,Schwab, Ricardo S.,Alberto, Eduardo E.,Salman, Syed M.,Vargas, Josimar,Azeredo, Juliano B.
scheme or table, p. 2309 - 2311 (2009/08/17)
A set of chiral β-seleno amines were prepared by the ring-opening reaction of unprotected aziridines. Under acid conditions diaryl or dialkyl diselenides were reduced by zinc and treated with unprotected aziridines to produce the desired products in good
Modular synthesis of chiral N-protected β-seleno amines and amides via cleavage of 2-oxazolidinones and application in palladium-catalyzed asymmetric allylic alkylation
Sehnem, Jasquer A.,Vargas, Fabricio,Milani, Priscila,Nascimento, Vanessa,Braga, Antonio L.
, p. 1262 - 1268 (2008/12/22)
A set of chiral β-seleno amines have been efficiently synthesized via the ring-opening reaction of chiral N-acyl oxazolidinones by selenium nucleophiles. These compounds could be transformed into β-seleno amides by reaction with acid chlorides. The presen
Straightforward synthesis of non-natural selenium containing amino acid derivatives and peptides
Braga, Antonio L.,Luedtke, Diogo S.,Paixao, Marcio W.,Alberto, Eduardo E.,Stefani, Helio A.,Juliano, Luiz
, p. 4260 - 4264 (2007/10/03)
A series of non-natural selenium-containing amino acid derivatives and peptides have been synthesized, in a flexible and modular strategy. The peptide coupling reaction between N-protected amino acids and chiral ss-seleno amines afforded the desired products in high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Seleno-imine: A new class of versatile, modular N,Se ligands for asymmetric palladium-catalyzed allylic alkylation
Braga, Antonio L.,Paix?o, Márcio W.,Marin, Graciane
, p. 1675 - 1678 (2007/10/03)
The palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate in the presence of chiral seleno-imine ligands derived from an inexpensive and easily available chiral pool was investigated. Excellent yield a
