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19.5.10.1.1.3 Variation 3: Using Trimethylsilyl Cyanide

DOI: 10.1055/sos-SD-019-00171

North, M.Science of Synthesis, (200419289.

Trimethylsilyl cyanide will add to imines,[‌35‌] iminium salts,[‌36‌] or a mixture of an aldehyde and an amine[‌37‌,‌38‌] to give an α-aminonitrile in each case. It is also possible to heat a mixture of trimethylsilyl cyanide, an aldehyde or ketone, and an amine to 100°C in a sealed vial, in the absence of a solvent and obtain a high yield of the resulting α-aminonitrile in less than two minutes, e.g. formation of 7 (Scheme 4).[‌39‌] Recently, the use of high pressure (600MPa) to induce the three-component condensation of a ketone, aromatic amine, and trimethylsilyl cyanide has been reported,[‌40‌] and was found to be particularly advantageous when sterically hindered ketones and amines were used as substrates.[‌41‌] Many Lewis acids will catalyze the addition of trimethylsilyl cyanide to imines, although zinc(II) iodide is most commonly used and will also catalyze the addition of trimethylsilyl cyanide to an imine generated in situ by the dehydrochlorination of an N-chloroamine.[‌42‌,‌43‌]

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Meeeeeee-Meeeeee Meeeeeeee ee α-Meeeeeeeeeeee 8; Meeeeee Meeeeeeee:[‌88‌]

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α-Meeeeeeeeeeee 8 Meeee Meeeeeeee Meeeeeeeeeeeeeeeeeeeeeeee; Meeeeee Meeeeeeee:[‌88‌]

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α-Meeeeeeeeeeee 8 Meeee Meeeeee Meeeeeeeeee; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

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References


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