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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.

SUBMITTER: Zhang JW

PROVIDER: S-EPMC4753251 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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

Zhang Ji-Wei JW Xu Jin-Hui JH Cheng Dao-Juan DJ Shi Chuan C Liu Xin-Yuan XY Tan Bin B

Nature communications 20160211

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 enant ...[more]

PMID: 26864510

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