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

Zhang, Zhipeng; Bae, Han Yong; Guin, Joyram; Rabalakos, C.; van Gemmeren, Manuel; Leutzsch, Markus; Klussmann, Martin; List, Benjamin

doi:10.1038/ncomms12478

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

MPS-Authors

/persons/resource/persons59139

Zhang, Zhipeng
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons199547

Bae, Han Yong
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58593

Guin, Joyram
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58906

Rabalakos, C.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58786

van Gemmeren, Manuel
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons132873

Leutzsch, Markus
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58702

Klussmann, Martin
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58764

List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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引用

Zhang, Z., Bae, H. Y., Guin, J., Rabalakos, C., van Gemmeren, M., Leutzsch, M., Klussmann, M., & List, B. (2016). Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes. Nature Communications, (7):. doi:10.1038/ncomms12478.

引用: https://hdl.handle.net/11858/00-001M-0000-002B-9DF6-6

要旨

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.