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


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.

SUBMITTER: Zhang Z 

PROVIDER: S-EPMC4992067 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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

Zhang Zhipeng Z   Bae Han Yong HY   Guin Joyram J   Rabalakos Constantinos C   van Gemmeren Manuel M   Leutzsch Markus M   Klussmann Martin M   List Benjamin B  

Nature communications 20160817


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, th  ...[more]

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