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

SYNTHESIS-STUTTGART(2021)

Cited 3|Views7
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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.
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Key words
julolidine, 1,5-hydride shift, redox-neutral reaction, tetrahydroquinoline, catalysis
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