Dehydrogenation of methyl 1,2,3,4-tetrahydroisoquinolin-2-yl- and β-carbolin-9-yl-acetates with palladium black in dimethylformamide generates anti-azomethine ylides stereospecifically. The analogous reaction with methyl isoindolin-2-ylacetate gives the corresponding isoindole. Both types of product can be trapped by N-methylmaleimide. The mechanism of the dehydrogenation processes is discussed.
R. Grigg and F. Heaney, J. Chem. Soc., Perkin Trans. 1, 1989, 198 DOI: 10.1039/P19890000198
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