57224-50-7Relevant articles and documents
A general asymmetric synthesis of artificial aliphatic and perfluoroalkylated α-amino acids by Luche's cross-electrophile coupling reaction
Gugkaeva, Zalina T.,Larionov, Vladimir A.,Maleev, Victor I.,Smol'yakov, Alexander F.
supporting information, p. 5327 - 5332 (2021/06/28)
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.
Stereoselective conjugate addition of organocuprates to a dehydroalanine derived diketopiperazine
Bull, Steven D.,Davies, Stephen G.,O'Shea, Michael D.
, p. 3657 - 3658 (2007/10/03)
An asymmetric synthesis of homochiral α-amino acids has been developed which is based on the conjugate addition of organocuprates to the dehydroalanine equivalent (3S)-N,N′-bis(p-methoxybenzyl)-3-isopropyl-6-methylenepiperazine-2,5-dione 6.
