2006
DOI: 10.1016/j.tetlet.2006.01.141
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Electrochemical oxidation of 2-substituted piperidines as a key step towards the synthesis of hydroxylated γ-amino acids

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Cited by 16 publications
(9 citation statements)
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“…Since the greatest conformational change involved the nitrogen atom in the piperidine ring to give 5 Å+ , it can be assumed that electron is virtually lost from the nitrogen atom [39,40]. A simile behavior has been previously reported for the electrochemical oxidation of the piperidinic ring in aqueous solution, where one hydroxyl is added in alpha or beta to the piperidinic nitrogen [41][42][43] in a 2 electrons oxidation process of the piperidinic ring with subsequent deprotonation and nucleophilic addition (e.g. water) was already Fig.…”
Section: Proposed Risperidone Oxidation Mechanism: Dft Approachmentioning
confidence: 85%
“…Since the greatest conformational change involved the nitrogen atom in the piperidine ring to give 5 Å+ , it can be assumed that electron is virtually lost from the nitrogen atom [39,40]. A simile behavior has been previously reported for the electrochemical oxidation of the piperidinic ring in aqueous solution, where one hydroxyl is added in alpha or beta to the piperidinic nitrogen [41][42][43] in a 2 electrons oxidation process of the piperidinic ring with subsequent deprotonation and nucleophilic addition (e.g. water) was already Fig.…”
Section: Proposed Risperidone Oxidation Mechanism: Dft Approachmentioning
confidence: 85%
“…For the electrochemical oxidation of the piperidinic ring in aqueous solution, a simile behavior has been reported in previous studies. [43][44][45] Other considerations that can further support the proposed mechanism can be found in literature. The imide groups are reducible but not oxidizable in the usual conditions and the lactone moiety is not oxidizable at the applied potentials.…”
Section: Proposed Ris Oxidation Mechanismmentioning
confidence: 95%
“…Moreover, the presence of the N-acryloyl group allowed for substrate postsynthetic modification through thiol conjugate addition or olefin cross-metathesis with a fluorescent dye (Scheme 17). 223 Electrochemical oxidation has also proven to be a viable strategy towards the synthesis of g-amino acids 224 and preparing peptidomimetics. [225][226][227][228][229][230][231][232][233][234][235] Schmalz and coworkers utilized the Shono oxidation in the context of accessing a tricyclic dipeptide mimetic (80) starting from L-proline (77).…”
Section: Shono-type Anodic Oxidationsmentioning
confidence: 99%