DEVELOPMENT OF METHOD FOR EFFICIENT alpha-OXIDATION OF tert-ALKYLAMINES USING BIS(2,2,2-TRICHLOROETHYL) AZODICARBOXYLATE

作者：Honzawa Shinobu^*; Uchida Mitsuaki; Sugihara Takumichi

来源：Heterocycles, 2014, 88(2): 975-980.

DOI：10.3987/COM-13-S(S)108

An efficient alpha-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 alpha-oxidation, and in the case of N-phenylpyrrolidine an interesting dimerization reaction is followed by alpha-oxidation. The alpha-oxidation product can be transformed in the presence of nucleophiles and a Lewis acid to alpha-modified amines, presumably via an iminium intermediate.

• 出版日期2014-1-1