Статья

Stereoselective synthesis of unnatural α-amino acid derivatives through photoredox catalysis

A. Shatskiy, A. Axelsson, E. Stepanova, J. Liu, A. Temerdashev, B. Kore, B. Blomkvist, J. Gardner, P. Dinér, M. Kärkäs,
2021

A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived N-sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids. The developed protocol allows the use of ubiquitous carboxylic acids as radical precursors without prior derivatization. The protocol utilizes near-stoichiometric amounts of the imine and the acid radical precursor in combination with a catalytic amount of an organic acridinium-based photocatalyst. Alternative mechanisms for the developed transformation are discussed and corroborated by experimental and computational studies.

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  • 1. Version of Record от 2021-04-21

Метаданные

Об авторах
  • A. Shatskiy
    The Royal Institute of Technology (KTH)
  • A. Axelsson
    The Royal Institute of Technology (KTH)
  • E. Stepanova
    Tomsk Polytechnic University, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
  • J. Liu
    The Royal Institute of Technology (KTH)
  • A. Temerdashev
    Kuban State University
  • B. Kore
    The Royal Institute of Technology (KTH)
  • B. Blomkvist
    The Royal Institute of Technology (KTH)
  • J. Gardner
    The Royal Institute of Technology (KTH)
  • P. Dinér
    The Royal Institute of Technology (KTH)
  • M. Kärkäs
    The Royal Institute of Technology (KTH)
Название журнала
  • Chemical Science
Том
  • 12
Выпуск
  • 15
Страницы
  • 5430-5437
Финансирующая организация
  • Tomsk Polytechnic University
Номер гранта
  • 203\2020
Тип документа
  • journal article
Тип лицензии Creative Commons
  • CC BY
Правовой статус документа
  • Свободная лицензия
Источник
  • scopus