Photocatalytic Asymmetric Acyl Radical Truce–Smiles Rearrangement for the Synthesis of Enantioenriched α‐Aryl Amides

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Abstract: The radical Truce–Smiles rearrangement is a straightforward strategy for incorporating aryl groups into organic molecules for which asymmetric processes remains rare. By employing a readily available and non‐expensive chiral auxiliary, we developed a highly efficient asymmetric photocatalytic acyl and alkyl radical Truce–Smiles rearrangement of α‐substituted acrylamides using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom–transfer photocatalyst, along with aldehydes or C−H containing precursors. The rearranged products exhibited excellent diastereoselectivities (7: 1 to >98: 2 d.r.) and chiral auxiliary was easily removed. Mechanistic studies allowed understanding the transformation in which density functional theory (DFT) calculations provided insights into the stereochemistry‐determining step.

Standort
Deutsche Nationalbibliothek Frankfurt am Main
Umfang
Online-Ressource
Sprache
Englisch

Erschienen in
Photocatalytic Asymmetric Acyl Radical Truce–Smiles Rearrangement for the Synthesis of Enantioenriched α‐Aryl Amides ; day:06 ; month:08 ; year:2024 ; extent:10
Angewandte Chemie ; (06.08.2024) (gesamt 10)

Urheber
Ma, Wei‐Yang
Leone, Matteo
Derat, Etienne
Retailleau, Pascal
Reddy, Chada Raji
Neuville, Luc
Masson, Géraldine

DOI
10.1002/ange.202408154
URN
urn:nbn:de:101:1-2408071424040.054875142670
Rechteinformation
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Letzte Aktualisierung
14.08.2025, 10:48 MESZ

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Beteiligte

  • Ma, Wei‐Yang
  • Leone, Matteo
  • Derat, Etienne
  • Retailleau, Pascal
  • Reddy, Chada Raji
  • Neuville, Luc
  • Masson, Géraldine

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