915405-01-5Relevant articles and documents
Selenoimidazolium Salts as Supramolecular Reagents for Protein Alkylation
Lim, David,Wen, Xiaojin,Seebeck, Florian P.
, p. 3515 - 3520 (2020/09/21)
Se-benzyl selenoimidazolium salts are characterized by remarkable alkyl-transfer potential under physiological conditions. Structure-activity relationship studies show that selective monoalkylation of primary amines depends on supramolecular interactions
Domino 1,3-dipolar cycloadditions of n- alkyl-α-amino esters with paraformaldehyde: A direct access to α-hydroxymethyl α-amino acids
Castelló, Luis M.,Nájera, Carmen,Sansano, José M.
, p. 967 - 971 (2014/04/03)
N-Alkyl-α-amino esters undergo a domino reaction, based on the iminium cation generation, with paraformaldehyde, followed by a 1,3-dipolar cycloaddition of the stabilized azomethA?ine ylide with another equivalent of formaldehyde. The resulting products are oxazolidines, which can be transformed after hydrolysis into α-hydroxymethyl α-amino acid or its derivatives. The diastereoselective 1,3-dipolar cycloaddition was performed using sarcosine (-)-menthyl or (-)-8-phenylmenthyl esters affording the cyclic product with moderate enantiomeric ratio. Georg Thieme Verlag Stuttgart · New York.
The facile production of N-methyl amino acids via oxazolidinones
Aurelio, Luigi,Brownlee, Robert T. C.,Hughes, Andrew B.,Sleebs, Brad E.
, p. 425 - 433 (2007/10/03)
A range of oxazolidinones derived from N-carbamoyl α-amino acids were prepared by an efficient method as key intermediates in the synthesis of N-methyl amino acids and peptides. The method was readily applied to most α-amino acids except those with basic side chains. The oxazolidinones were converted by reductive cleavage into N-methyl α-amino acids. CSIRO 2000.
General method for the synthesis of N-methyl amino acids and N-alkyl amino esters from O'Donnell's Schiff bases
Chruma, Jason J.,Sames, Dalibor,Polt, Robin
, p. 5085 - 5086 (2007/10/03)
N-methyl amino acids, including L-abrine, and N-alkyl amino esters, were synthesized by reductive amination of O'Donnell's Schiff base amino esters with NaBH3CN and formaldehyde, or the appropriate aldehyde in CH3CN or THF in good to excellent yields, and with high purity.
Etude par la Modelisation Moleculaire de la Regioselectivite de l'Ouverture des Acides Glycidiques par les Amines Aliphatiques
Grosjean, F.,Huche, M.,Larcheveque, M.,Legendre, J. J.,Petit, Y.
, p. 9325 - 9334 (2007/10/02)
A model for glycidic acids opening reaction by ammonia and amines has been suggested from semi-empiric orbital calculations.It provides a way for evaluating the different interactions between the incoming nucleophile and the oxirane substituents.Steric and coulombic interactions of the carboxylate in staggered conformation (cis substitution) has a major influence to rationalize experimental regioselectivity.
