Fig. 2: Rational design of N-alkylpyridinium reagents. | Nature Communications

Fig. 2: Rational design of N-alkylpyridinium reagents.

From: Chemoselective dual functionalization of proteins via 1,6-addition of thiols to trifunctional N-alkylpyridinium

Fig. 2

a Fukui indices for (E)-3-(pyridin-4-yl)acrylic acid, after quaternization of the nitrogen atom and amide formation reveals increasing selectivity for 1,6-addition (pink) over the more common 1,4-addition (blue). b Model reaction showing the 1,6- and 1,4-addition of thiols to compound 1, respectively. c Synthetic route of the various N-alkylpyridinium derivatives (1–6, yields up to 60% overall steps). N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide (EDC), 4-Dimethylaminopyridine (DMAP).

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