A general asymmetric synthesis of artificial aliphatic and perfluoroalkylated α-amino acids by Luche's cross-electrophile coupling reaction

Aliphatic artificial α-amino acids (α-AAs) have attracted great interest in biochemistry and pharmacy. In this context, we developed a promising practical protocol for the asymmetric synthesis of these α-AAs through the selective and efficient intermolecular cross-electrophile coupling of Belokon's chiral dehydroalanine Ni(ii) complex with different alkyl and perfluoroalkyl iodides mediated by a dual Zn/Cu system. The reaction afforded diastereomeric complexes with dr up to 21.3 : 1 in 24-95% yields (19 examples). Exemplarily, three enantiomerically pure aliphatic α-AAs were obtained through acidic decomposition of (S,S)-diastereomers of Ni(ii) complexes. Importantly, the chiral auxiliary ligand (S)-BPB((S)-2-(N-benzylprolyl)aminobenzophenone) was easily recycled by simple filtration after acidic complex decomposition and reused for the synthesis of the initial dehydroalanine Ni(ii) complex. © The Royal Society of Chemistry 2021.

Publisher
Royal Society of Chemistry
Number of issue
24
Language
English
Pages
5327-5332
Status
Published
Volume
19
Year
2021
Organizations
  • 1 A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilov Str. 28, Moscow, 119991, Russian Federation
  • 2 Plekhanov Russian University of Economics, Stremyanny per. 36, Moscow, 117997, Russian Federation
  • 3 Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya Str. 6, Moscow, 117198, Russian Federation
Date of creation
20.07.2021
Date of change
20.07.2021
Short link
https://repository.rudn.ru/en/records/article/record/74192/
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