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1,5-Hydride-Shift-Triggered Cyclization for the Synthesis of Unsymmetric Julolidines

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Directly accessible 8-substituted tetrahydroquinolines undergo 1,5-hydride-shift-triggered cyclization to provide difficult to access julolidine derivatives in yields of 21–98% under scandium(III) triflate catalysis. Additionally, the scope of the reaction, several follow-up… Click to show full abstract

Directly accessible 8-substituted tetrahydroquinolines undergo 1,5-hydride-shift-triggered cyclization to provide difficult to access julolidine derivatives in yields of 21–98% under scandium(III) triflate catalysis. Additionally, the scope of the reaction, several follow-up transformations and a remarkable side process discovered during optimization of the conditions are highlighted.

Keywords: shift triggered; hydride shift; triggered cyclization; synthesis unsymmetric; cyclization synthesis

Journal Title: Synthesis
Year Published: 2021

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