title: Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction.
abstract: Axially chiral compounds play an important role in areas such as asymmetric catalysis. The tyrosine click-like reaction is an efficient approach for synthesis of urazoles with potential applications in pharmaceutical and asymmetric catalysis. Here we discover a class of urazole with axial chirality by restricted rotation around an N-Ar bond. By using bifunctional organocatalyst, we successfully develop an organocatalytic asymmetric tyrosine click-like reaction in high yields with excellent enantioselectivity under mild reaction conditions. The excellent remote enantiocontrol of the strategy originates from the efficient discrimination of the two reactive sites in the triazoledione and transferring the stereochemical information of the catalyst into the axial chirality of urazoles at the remote position far from the reactive site.
authors: Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055, China.
authors: Ji-Wei
authors: JW
authors: Zhang
authors: Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055, China.
authors: Jin-Hui
authors: JH
authors: Xu
authors: Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055, China.
authors: Dao-Juan
authors: DJ
authors: Cheng
authors: Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055, China.
authors: Chuan
authors: C
authors: Shi
authors: Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055, China.
authors: Xin-Yuan
authors: XY
authors: Liu
authors: Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055, China.
authors: Bin
authors: B
authors: Tan
mesh_terms: D002384:Catalysis; D002855:Chromatography, Thin Layer; D057930:Click Chemistry; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis*; D014443:Tyrosine / Q000378:metabolism*
chemical_list: D014230:Triazoles; D014443:Tyrosine; C421465:urazole