Science of Synthesis

Leclerc, E., Science of Synthesis Knowledge Updates, (2024) 3, 257.

The cyanosulfurylide group was recently introduced as a protecting group for carboxylic acids, with a particular emphasis on the protection of a carboxy group on the side chain of amino acids.[‌34‌] The cyanosulfurylide group can be introduced by the reaction of the carboxylic acid with (cyanomethyl)dimethylsulfonium bromide in the presence of propylphosphonic anhydride (T3P) as a base, and it can later be cleaved with N-chlorosuccinimide under mild conditions to reform the carboxylic acid, e.g. ‌19‌ (‌Scheme 16‌).

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