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Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes

Author

Listed:
  • Zhipeng Zhang

    (Max-Planck-Institut für Kohlenforschung)

  • Han Yong Bae

    (Max-Planck-Institut für Kohlenforschung)

  • Joyram Guin

    (Max-Planck-Institut für Kohlenforschung)

  • Constantinos Rabalakos

    (Max-Planck-Institut für Kohlenforschung)

  • Manuel van Gemmeren

    (Max-Planck-Institut für Kohlenforschung)

  • Markus Leutzsch

    (Max-Planck-Institut für Kohlenforschung)

  • Martin Klussmann

    (Max-Planck-Institut für Kohlenforschung)

  • Benjamin List

    (Max-Planck-Institut für Kohlenforschung)

Abstract

Due to the high versatility of chiral cyanohydrins, the catalytic asymmetric cyanation reaction of carbonyl compounds has attracted widespread interest. However, efficient protocols that function at a preparative scale with low catalyst loading are still rare. Here, asymmetric counteranion-directed Lewis acid organocatalysis proves to be remarkably successful in addressing this problem and enabled a molar-scale cyanosilylation in quantitative yield and with excellent enantioselectivity. Also, the catalyst loading could be lowered to a part-per-million level (50 ppm: 0.005 mol%). A readily accessible chiral disulfonimide was used, which in combination with trimethylsilyl cyanide, turned into the active silylium Lewis acid organocatalyst. The nature of a peculiar phenomenon referred to as a “dormant period”, which is mainly induced by water, was systematically investigated by means of in situ Fourier transform infrared analysis.

Suggested Citation

  • Zhipeng Zhang & Han Yong Bae & Joyram Guin & Constantinos Rabalakos & Manuel van Gemmeren & Markus Leutzsch & Martin Klussmann & Benjamin List, 2016. "Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes," Nature Communications, Nature, vol. 7(1), pages 1-8, November.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms12478
    DOI: 10.1038/ncomms12478
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    Cited by:

    1. Guodong Fan & Qingyun Wang & Jun Xu & Pengcheng Zheng & Yonggui Robin Chi, 2023. "Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles," Nature Communications, Nature, vol. 14(1), pages 1-8, December.

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