Asymmetric Metal-Templated Route to Amino Acids with an Isoquinolone Core via a Rh(III)-Catalyzed Coupling of Aryl Hydroxamates with Chiral Propargylglycine Ni(II) ComplexesстатьяИсследовательская статья
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Аннотация:A general protocol for the asymmetric synthesis of artificial amino acids (AAs) comprising an isoquinolone skeletal was successfully elaborated via a straightforward Rh(III)-catalyzed C−H activation/annulation of various aryl hydroxamates with a series of robust chiral propargylglycine Ni(II) complexes derived from glycine (Gly), alanine (Ala) and phenylalanine (Phe) in green solvent (methanol) and under mild conditions (at room temperature under air atmosphere). Notably, in the case of phenylalanine-derived complexes, the formation of unfavorable 4-substituted isoquinolone regioisomers was achieved by a catalyst control for the first time. The subsequent acidic decomposition of the obtained Ni(II) complexes provides the target unnatural α- and α,α-disubstituted AAs with an isoquinolone core in an enantiopure form.