Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes
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- Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes
- Zhang, Zhipeng; Bae, Han Yong; Guin, Joyram; Rabalakos, Constantinos; van Gemmeren, Manuel; Leutzsch, Markus; Klussmann, Martin; List, Benjamin
- Issue Date
- NATURE PUBLISHING GROUP
- NATURE COMMUNICATIONS, v.7, no., pp.12478 -
- 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.
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