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Catalytic asymmetric C–Si bond activation via torsional strain-promoted Rh-catalyzed aryl-Narasaka acylation

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  • Jia Feng

    (University of Science and Technology of China)

  • Xiufen Bi

    (University of Science and Technology of China)

  • Xiaoping Xue

    (University of Science and Technology of China)

  • Na Li

    (University of Science and Technology of China)

  • Lei Shi

    (University of Science and Technology of China)

  • Zhenhua Gu

    (University of Science and Technology of China
    Minjiang University)

Abstract

Atropisomers are important organic frameworks in bioactive natural products, drugs as well as chiral catalysts. Meanwhile, silanols display unique properties compared to their alcohol analogs, however, the catalytic synthesis of atropisomers bearing silanol groups is challenging. Here, we show a rhodium-catalyzed torsional strain-promoted asymmetric ring-opening reaction for the synthesis of α-silyl biaryl atropisomers. The reaction features a dynamic kinetic resolution of C(Ar)-Si bond cleavage, whose stereochemistry was controlled by a phosphoramidite ligand derived from (S)-3-methyl-1-((2,4,6-triisopropylphenyl)sulfonyl)piperazine. This work is a demonstration of an aryl-Narasaka acylation, where the C(Ar)-Si bond cleavage is promoted by the torsional strain of α, α’-disubstituted silafluorene.

Suggested Citation

  • Jia Feng & Xiufen Bi & Xiaoping Xue & Na Li & Lei Shi & Zhenhua Gu, 2020. "Catalytic asymmetric C–Si bond activation via torsional strain-promoted Rh-catalyzed aryl-Narasaka acylation," Nature Communications, Nature, vol. 11(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-18273-3
    DOI: 10.1038/s41467-020-18273-3
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