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Paper | Special issue | Vol 99, No. 1, 2019, pp.248-266
Published online, 13th August, 2018
DOI: 10.3987/COM-18-S(F)18
Indium Mediated Allylation of N-tert-Butanesulfinyl Imines with 1,3-Dibromopropene: Stereoselective Synthesis of Aziridines

Edgar Maciá, Francisco Foubelo,* and Miguel Yus*

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99 03080 Alicante, Spain

Abstract

The reaction of N-tert-butanesulfinyl imines 1 with 1,3-dibromopropene (2), in the presence of indium metal, in saturated aqueous solution of sodium bromide, produced bromohomoallylamine derivatives 3 with total facial diastereoselectivity for the imine addition, and moderate yields. These compounds were easily transformed into the corresponding vinyl aziridines 5 upon deprotonation with KHMDS in THF, the intramolecular cyclization taking place in a stereospecific manner in moderate to high yields.