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

Zhipeng Zhang, Han Yong Bae, Joyram Guin, Constantinos Rabalakos, Manuel van Gemmeren, Markus Leutzsch, Martin Klussmann and Benjamin List ()
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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

Nature Communications, 2016, vol. 7, issue 1, 1-8

Abstract: 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.

Date: 2016
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DOI: 10.1038/ncomms12478

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