35150-07-3Relevant articles and documents
Synthetic Studies on Alotamide A: Construction of N-Demethylalotamide A
Domínguez, Marta,Román, David,Souto, José A.,de Lera, ángel R.
supporting information, p. 6057 - 6070 (2021/12/10)
Several approaches to the synthesis of cyclodepsipeptide natural product alotamide A are described, eventually affording a very advanced N-demethylated analogue of the targeted natural product. The difficulties found in our endeavors on the synthesis of alotamide A have allowed us to gather some valuable information regarding the most convenient synthetic step for each key transformation. The intramolecular Csp2?Csp2 Stille cross-coupling and the macrolactam formation were found to be reliable protocols for the final construction of the alotamide A skeleton.
Process Development of a Copper(II)-Catalyzed Dehydration of an N -Acyl Prolinal Oxime: Cascade Process and Application at an Elevated Lab Scale
Nonnhoff, Jannis,Gr?ger, Harald
supporting information, p. 4672 - 4677 (2021/10/07)
Chiral N-acyl amino nitriles are important structural motifs in several pharmaceuticals such as Vildagliptin or Saxagliptin. Cyanidefree access to such nitriles is provided by a copper-catalyzed dehydration of oximes, which are readily available by condensation of chiral aldehydes resulting from the chiral pool with hydroxylamine. The application in a cascade process without the need for intermediate purification as well as a demonstrated scalability show the robustness of this methodology.
Evidence and exploitation of dicationic ammonium-nitrilium superelectrophiles: direct synthesis of unsaturated piperidinones
Cantin, Thomas,Morgenstern, Yvonne,Mingot, Agnès,Kornath, Andreas,Thibaudeau, Sébastien
supporting information, p. 11110 - 11113 (2020/10/05)
Exploiting superacid activation, the reactivity of aminonitriles was enhanced through the transient formation of highly reactive ammonium-nitrilium superelectrophiles. Demonstrated by usingin situlow-temperature NMR experiments and confirmed by X-ray diffraction analysis, these dications can be intramolecularly trapped by non-activated alkenes to generate unsaturated piperidinones, including enantioenriched ones, in a straightforward way.
