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

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

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

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

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

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

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

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

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

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Citation

Zhang, Z., Bae, H. Y., Guin, J., Rabalakos, C., van Gemmeren, M., Leutzsch, M., et al. (2016). Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes. Nature Communications, 7: 12478. doi:10.1038/ncomms12478.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002B-9DF6-6
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.