119506-92-2Relevant academic research and scientific papers
Base-promoted c→n acyl rearrangement: An unconventional approach to α-amino acid derivatives
Ugarriza, Iratxe,Uria, Uxue,Carrillo, Luisa,Vicario, Jose L.,Reyes, Efraim
supporting information, p. 11650 - 11654 (2014/10/15)
We have discovered that N-alkyl aminomalonates undergo a fast and selective intramolecular C→N acyl rearrangement reaction in the presence of a strong base, leading to N-protected glycinates in excellent yield. Moreover, the fact that the reaction proceeds through a nucleophilic enolate intermediate has been used for implementing a tandem rearrangement/alkylation sequence that has been applied to the preparation of synthetically relevant nonproteinogenic tertiary and quaternary N-alkyl α-amino acids in a very simple and reliable way.
Bis(methoxycarbonyl)carbene Insertion into N-H Bonds: A Facile Route to N-Substituted Aminomalonic Esters
Husinec, Suren,Juranic, Ivan,Llobera, Antonia,Porter, Alexander E. A.
, p. 721 - 723 (2007/10/02)
Bis(methoxycarbonyl)carbene, generated by the cooper(II)-catalyzed fragmentation of 2,5-dichlorothiophenium-1-bis(methoxycarbonyl)methylide (3) undergoes rapid and efficient insertion into the N-H bonds of primary and secondary amines to generate N-substi
