C-N cross coupling reactions play a vital role in the construction of many important organic intermediates and biologically active compounds. The ability of diaryliodonium salts in C-N cross coupling reactions pave the way for the rapid N-arylation of sulfoximines under eco-friendly conditions. The transformation was achieved by reacting sulfoximines with diaryliodonium salts in aqueous polyethylene glycol-400 using CuBr as catalyst under ultrasonic conditions (Scheme 1) Unnatural amino acids have high value in drug discovery and development. Herein, we present the first report of a new class of unnatural a-amino acids bearing a dithiocarbamate side chain. These unnatural a-amino acids containing the dithiocarbamate side chain were synthesized via a one-pot, regio- and stereo-selective ring opening of sulfamidates by dithiocarbamate anions (generated in-situ) in aerial atmosphere without any special precaution and in absence of any catalyst/additive (Scheme 2).

Benign synthesis of N-aryl sulfoximines and unnatural amino acids with dithiocarbamate side chain

244th National Meeting (2012)

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