56599-00-9Relevant 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.
SIMPLE AND CONDENSED β-LACTAMS-I. THE APPLICATION OF DIKETENE IN β-LACTAM SYNTHESIS. THE SYNTHESIS AND FUNCTIONAL GROUP MANIPULATIONS OF DIETHYL 3-ACETYL-4-OXOAZETIDINE-2,2-DICARBOXYLATES
Simig, Gyula,Doleschall, Gabor,Hornyak, Gyula,Fetter, Jozsef,Lempert, Karoly,et al.
, p. 479 - 484 (2007/10/02)
Acetylation of the N-substituted diethyl aminomalonates 3a-3d with diketene furnished the ring tautomers 6a-6d of the expected acetoacetyl derivatives 5.By treatment with iodine and sodium ethoxide compounds 6a-6d are smoothly converted into the β-lactam
