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Communication | Special issue | Vol 88, No. 2, 2014, pp.975-980
Published online, 13th September, 2013
DOI: 10.3987/COM-13-S(S)108
Development of Method for the Efficient α-Oxidation of tert-Alkylamines Using bis(2,2,2-Trichloroethyl) Azodicarboxylate

Shinobu Honzawa,* Mitsuaki Uchida, and Takumichi Sugihara*

*Department of Pharmaceutical Sciences, Niigata University of Pharmacy and Applied Life Sciences, 265-1, Higashi-jima, Akiha-ku, Niigata 956-8603, Japan

Abstract

An efficient α-oxidation of amines can be accomplished using bis(2,2,2-trichloroethyl) azodicarboxylate, which is more electrophilic than diethyl azodicarboxylate, often used in synthetic chemistry. N-Acetyl and N-tert-butoxycarbonylamines are good substrates for this α-oxidation, and in the case of N-phenylpyrrolidine an interesting dimerization reaction is followed by α-oxidation. The α-oxidation product can be transformed in the presence of nucleophiles and a Lewis acid to α-modified amines, presumably via an iminium intermediate.