ol8b02967_si_001.pdf (5.33 MB)
An Amine Group Transfer Reaction Driven by Aromaticity
journal contribution
posted on 2018-10-26, 13:20 authored by Sebastian Ahles, Silas Götz, Luca Schweighauser, Mirko Brodsky, Simon N. Kessler, Andreas H. Heindl, Hermann A. WegnerA 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.