Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction

Ji-Wei Zhang, Jin-Hui Xu, Dao-Juan Cheng, Chuan Shi, Xin-Yuan Liu () and Bin Tan ()
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Ji-Wei Zhang: South University of Science and Technology of China
Jin-Hui Xu: South University of Science and Technology of China
Dao-Juan Cheng: South University of Science and Technology of China
Chuan Shi: South University of Science and Technology of China
Xin-Yuan Liu: South University of Science and Technology of China
Bin Tan: South University of Science and Technology of China

Nature Communications, 2016, vol. 7, issue 1, 1-10

Abstract: 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.

Date: 2016
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DOI: 10.1038/ncomms10677

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