Nature research paper: Organocatalytic stereoselective cyanosilylation of small ketones
On the basis of the accumulated experimental, spectroscopic and computational data, we can now propose a mechanism for the cyanosilylation of ketones enabled by IDPi catalysts. Accordingly, the initial silylation of the catalyst with TMSCN generates the silylated catalyst, which—in turn—activates the ketone to furnish a silyloxy carbenium intermediate, which can be readily deprotonated by the chiral anion of the catalyst to provide the corresponding enol silanes under the reaction conditions .
In conclusion, we show that properly designed chiral and confined acids can catalyse an asymmetric cyanosilylation reaction of both aromatic and aliphatic ketones, including the highly challenging 2-butanone. Our work can serve as an encouragement for chemists to create catalysts that rival the remarkable and sometimes extreme selectivities observed with enzymes. We also anticipate that our method could be of use in the synthesis of natural products and pharmaceuticals.
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