NHC-catalyzed atropoenantioselective synthesis of axially chiral biaryl amino alcohols via a cooperative strategy

Gongming Yang, Donghui Guo, Di Meng and Jian Wang ()
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Gongming Yang: Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University
Donghui Guo: Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University
Di Meng: Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University
Jian Wang: Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University

Nature Communications, 2019, vol. 10, issue 1, 1-6

Abstract: Abstract Axially chiral biaryl amino-alcohols play a pivotal role in organic synthesis and drug discovery. However, only a very few enantioselective methods have been reported to synthesize chiral biaryl amino-alcohols. Therefore, the rapid enantioselective construction of optically active biaryl amino-alcohols still remains a formidable challenge. Here we report an N-heterocyclic carbene (NHC)-catalyzed atropoenantioselective acylation of biphenols triggered by a cooperative strategy consisting of desymmetrization followed by kinetic resolution. This protocol features broad substrate scope and good functional group tolerance, and allows for a rapid construction of axially chiral biaryl amino-alcohols in good to high yields and with excellent enantioselectivities. Furthermore, the structurally diverse axially chiral biaryl amino-alcohol derivatives provide multiple possibilities for chemists to develop catalysts or ligands for different chemical transformations.

Date: 2019
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DOI: 10.1038/s41467-019-10878-7

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