88452-79-3Relevant academic research and scientific papers
Synthesis of α-amino acids by reaction of aziridine-2-carboxylic acids with carbon nucleophiles
Beresford, Kenneth J. M.,Church, Nicola J.,Young, Douglas W.
, p. 2888 - 2897 (2008/02/08)
A variety of homochiral α-amino acids have been prepared in good yield via regioselective reaction of higher order cuprates with (2S)-N-para-toluenesulfonylaziridine-2-carboxylic acid 4. The reaction was much less regioselective and low yielding when higher order cuprates were reacted with the more hindered aziridine carboxylic acid 30, the principal products being protected β-amino acids. Reaction of lithium trimethylsilylacetylide with the aziridine acid 30, however, gave a protected α-amino acid which was converted to the protected isoleucine ester 37. The Royal Society of Chemistry 2006.
Novel chiral dirhodium catalysts derived from aziridine and azetidine carboxylic acid for intermolecular cyclopropanation reactions with methyl phenyldiazoacetate
Starmans, Wim A. J.,Thijs, Lambertus,Zwanenburg, Binne
, p. 629 - 636 (2007/10/03)
Three new chiral dirhodium(II) tetracarboxylate catalysts, based on azetidine- and aziridine-2-carboxylic acid, were prepared. Their selectivities in the cyclopropanation reaction of methyl phenyl-diazoacetate and olefins were determined in solvents of de
Reduction of 2-acylaziridines by samarium(II) iodide. An efficient and regioselective route to β-amino carbonyl compounds
Molander, Gary A.,Stengel, Peter J.
, p. 8887 - 8912 (2007/10/03)
A convenient method for the reduction of 2-acylaziridines, aziridine-2- carboxylates and aziridine-2-carboxamides is described. The reduction of all of the substrates examined was extremely rapid and highly regioselective, giving rise to β-amino carbonyl compounds. This method appears to be general for all of the classes of aziridines mentioned above, and also tolerates a variety of nitrogen protecting groups.
Synthesis of α-Amino Acids by Ring Opening of Aziridine-2-carboxylates with Carbon Nucleophiles
Church, Nicola J.,Young, Douglas W.
, p. 151 - 154 (2007/10/02)
Excellent regiospecificity has been achieved in the reaction of carbon nucleophiles with N-para-toluenesulfonylaziridine-2-carboxylic acid (6, R=H) protected as the anion.This has been developed into a general and high yielding synthesis of optically pure α-amino acids containing one chiral centre.When the aziridine (20) containing a second chiral centre was used, only lithium trimethylsilylacetylide gave the desired α-amino acid.Reaction with higher order cuprates gave lower yields, the principal products being the protected β-amino acids (22) and (23).
