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

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.

Key words

julolidine - 1,5-hydride shift - redox-neutral reaction - tetrahydroquinoline - catalysis

Publication History

Received: 31 May 2021

Accepted after revision: 27 July 2021

Accepted Manuscript online:
27 July 2021

Article published online:
30 August 2021

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