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An Amine Group Transfer Reaction Driven by Aromaticity

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journal contribution
posted on 26.10.2018 by Sebastian Ahles, Silas Götz, Luca Schweighauser, Mirko Brodsky, Simon N. Kessler, Andreas H. Heindl, Hermann A. Wegner
A stereoselective domino inverse electron-demand Diels–Alder/amine group transfer reaction catalyzed by a bidentate Lewis acid provides 1-amino-1,2-dihydronaphthalenes, a core structure in many bioactive compounds. A concerted mechanism is proposed based on experimental studies as well as DFT computations demonstrating a new general reactivity scheme. The broad scope of the reaction was evaluated by variation of all three starting compounds, phthalazines, aldehydes, and amines. Scalability was demonstrated by a gram scale reaction without diminished yield.