An Amine Group Transfer Reaction Driven by Aromaticity
journal contributionposted on 26.10.2018 by Sebastian Ahles, Silas Götz, Luca Schweighauser, Mirko Brodsky, Simon N. Kessler, Andreas H. Heindl, Hermann A. Wegner
Any type of content formally published in an academic journal, usually following a peer-review process.
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.