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Communication | Special issue | Vol 99, No. 1, 2019, pp.93-99
Published online, 9th August, 2018
DOI: 10.3987/COM-18-S(F)19
Diastereoselective Synthesis of 5-Iodoalkenyl-2-oxazolines by Electrophilic Cyclization of Allenyl Amides

Tsukasa Hirokane, Ayaka Kawakami, Kenji Matsumoto, and Masahiro Yoshida*

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Nishihamabouji, Yamashiro-cho, Tokushima, 770-8514, Japan

Abstract

The electrophilic cyclization of allenyl amides is described. Allenyl amides were easily prepared from the propargyl aziridines via the [1,5]-hydrogen shift followed by the conversion of the imine moiety to the amides. 5-Iodoalkenyl-2-oxazolines having a variety of substituents were diastereoselectively obtained by the reaction of the allenyl amides with iodine.