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Transition‐Metal‐Free Deconstructive Lactamization of Piperidines by Julio Romero‐Ibañez; Silvano Cruz‐Gregorio; Jacinto Sandoval‐Lira; Julio M. Hernández‐Pérez; Leticia Quintero; Fernando Sartillo‐Piscil is a Chemistry article available to read on EtoBox.
What is Transition‐Metal‐Free Deconstructive Lactamization of Piperidines about?
One of the major challenges in organic synthesis is the activation or deconstructive functionalization of unreactive C(sp )-C(sp ) bonds, which requires using transition or precious metal catalysts. We present here an alternative: the deconstructive lactamization of piperidines without using transition metal catalysts. To this end, we use 3-alkoxyamino-2-piperidones, which were prepared from piperidines through a dual C(sp )-H oxidation, as transitory intermediates. Experimental and theoretical studies confirm that this unprecedented lactamization occurs in a tandem manner involving an oxidative deamination of 3-alkoxyamino-2-piperidones to 3-keto-2-piperidones, followed by a regioselective Baeyer-Villiger oxidation to give N-carboxyanhydride intermediates, which finally undergo a spontaneous and concerted decarboxylative intramolecular translactamization.
Who reads Transition‐Metal‐Free Deconstructive Lactamization of Piperidines?
It is typically read by researchers, students, and practitioners in Chemistry.
- Author
- Julio Romero‐Ibañez; Silvano Cruz‐Gregorio; Jacinto Sandoval‐Lira; Julio M. Hernández‐Pérez; Leticia Quintero; Fernando Sartillo‐Piscil
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley; Research Square (ISSN 0044-8249)
- Published
- 2019
- Language
- EN
- Field
- Chemistry (Physical Sciences)