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1‑(N‑Acylamino)alkyl Sulfones from N‑Acyl-α-amino Acids or N‑Alkylamides

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journal contribution
posted on 21.03.2014 by Jakub Adamek, Roman Mazurkiewicz, Agnieszka Październiok-Holewa, Mirosława Grymel, Anna Kuźnik, Katarzyna Zielińska
A variety of N-(1-methoxyalkyl)­amides or carbamates react readily with sodium aryl sulfinates in the presence of triphenylphosphonium tetrafluoroborate or bromide in CHCl3 under mild conditions to give 1-(N-acylamino)­alkyl sulfones in good yields. A combination of this reaction with the recently described electrochemical decarboxylative α-methoxylation of N-acyl-α-amino acids to give N-(1-methoxyalkyl)­amides in the presence of 3-(1-piperidino)­propyl-functionalized silica gel (SiO2–Pip) enables an effective two-pot transformation of N-acyl-α-amino acids to 1-(N-acylamino)­alkyl sulfones. Alternatively, N-(1-methoxyalkyl)­amides can be obtained by electrochemical α-methoxylation of either N-alkylamides, lactams, or N-alkylcarbamates.