Asymmetric Synthesis of Perfluoroalkylated α-Amino Acids through Generated Radicals Using a Chiral Ni(II) Complexстатья
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Дата последнего поиска статьи во внешних источниках: 20 января 2021 г.
Аннотация:Perfluoroalkylated α-amino acids (PFAAs) are a unique class of compounds for biochemistry and pharmaceutical science. In this context, we report the successful intermolecular coupling of the Belokon’s chiral dehydroalanine Ni(II) complex with a variety of perfluoroalkyl iodides. A 4-cyanopyridine/B2Pin2 catalytic system generates perfluoroalkyl radicals, which after trapping by the ligand sphere of a chiral Ni(II) complex provide the diastereomeric complexes with up to >20:1 dr (7 examples). The obtained major (S,S)-diastereomers were easily isolated by simple silica column chromatography in 33–54% yields. The perfluoroalkyl α-AAs were subsequently released from the obtained Ni(II) complexes via aqueous HCl treatment. The chiral auxiliary ligand ((S)-BPB = (S)-2-(N-benzylprolyl)aminobenzophenone) can be easily recycled after the acidic complex decomposition and reused for the synthesis of the starting dehydroalanine Ni(II) complex.