Work

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

Year: 2016

Type: article

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.

Source: Nature Communications

DOI: 10.1038/ncomms10677

Authors: Ji-Wei Zhang, Jin-Hui Xu, Dao-Juan Cheng, Chuan Shi, Xin-Yuan Liu, Bin Tan

Institution: Southern University of Science and Technology

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $6,990

Funder: National Natural Science Foundation of China