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Short Paper | Special issue | Vol 101, No. 1, 2020, pp.363-372
Published online, 11th September, 2019
DOI: 10.3987/COM-19-S(F)33
Construction of Quaternary Carbon Center by the Reaction of Aza-o-Quinone Methide Mediated Carbocation Intermediate

Yukiko Karuo, Shintaro Dousei, Minori Sakamoto, Atsushi Tarui, Kazuyuki Sato, Kentaro Kawai, and Masaaki Omote*

*Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata-shi, Osaka 573-0101 , Japan

Abstract

Reactions of carbocationic intermediate corresponding to aza-o-quinone methide with indoles to construct quaternary carbon center were described. Treatment of N-tosylated 2-(2-aminophenyl)propan-2-ol with iron(III) chloride provided tertiary benzylic carbocation intermediate possible to isomerize to the corresponding aza-o-quinone methide. The electron-deficient intermediate enabled to undergo nucleophilic attack by indoles, representing the first example of intermolecular formation of quaternary carbon center using aza-o-quinone methide mediated carbocation intermediate.