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On February 18, Xu Minghua's research group at the Shanghai Institute of Materia Medica, Chinese Academy of Sciences said that its self-designed simple phosphorene, a new open-chain structure, is a chiral ligand, and it has successfully realized the highly enantioselective synthesis of a series of 1,2,5-thiadiazolinone compounds containing quaternary carbon chirality in the rhodium-catalyzed boric acid asymmetric arylation reaction of 4-aryl-3-carbonyl-1,2,5-thiadiazole substrates and their derivatives.
After simple ring opening, the product can obtain structurally important various aryl substituted optically active aminoamides and isoindolinolins and isoindolinones
.
Due to the particularity of its structure, some efficient methods for synthesizing chiral unnatural amino acids, such as asymmetric hydrogenation, cannot be used to construct chiral quaternary carbon amino acid compounds
.
The method designed by this research group is simple to operate, mild conditions, high stereoselectivity and wide range of substrates, which provides the possibility
for chiral diaryl amino acid compounds to be used in related drug research in the future.
At present, the method has been successfully used in the first catalytic asymmetric synthesis
of BACE-1 inhibitor (R)-iminohydantoin (Ki79nm) reported by Merck.