- General method for the synthesis of N-methyl amino acids and N-alkyl amino esters from O'Donnell's Schiff bases
-
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.
- Chruma, Jason J.,Sames, Dalibor,Polt, Robin
-
-
Read Online
- Selenoimidazolium Salts as Supramolecular Reagents for Protein Alkylation
-
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
- Lim, David,Wen, Xiaojin,Seebeck, Florian P.
-
p. 3515 - 3520
(2020/09/21)
-
- Domino 1,3-dipolar cycloadditions of n- alkyl-α-amino esters with paraformaldehyde: A direct access to α-hydroxymethyl α-amino acids
-
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.
- Castelló, Luis M.,Nájera, Carmen,Sansano, José M.
-
p. 967 - 971
(2014/04/03)
-
- The facile production of N-methyl amino acids via oxazolidinones
-
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.
- Aurelio, Luigi,Brownlee, Robert T. C.,Hughes, Andrew B.,Sleebs, Brad E.
-
p. 425 - 433
(2007/10/03)
-