A General Asymmetric Synthesis of Artificial Aliphatic and Perfluoroalkylated α-Amino Acids by Luche’s Cross-Electrophile Coupling ReactionстатьяНаучно-популярная статья
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Дата последнего поиска статьи во внешних источниках: 1 июля 2021 г.
Аннотация:Aliphatic artificial α-amino acids (α-AAs) have a 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 the Belokon’s chiral dehydroalanine Ni(II) complex with different alkyl and perfluoroalkyl iodides mediated by a dual Zn/Cu system. The reaction afforded to the diastereomeric complexes with up to dr 21.3:1 in 24–95% yields (19 examples). Exemplary, the three enantiomerically pure aliphatic α-AAs were obtained through acidic decomposition of (S,S)-diastereomers of the 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.