Continuous-flow catalytic hydrogenation of 3a,6-epoxyisoindoles
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- Zaytsev, V.P., Zubkov, F.I., Mertsalov, D.F. et al. Russ Chem Bull (2015) 64: 112. doi:10.1007/s11172-015-0829-2
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Selective catalytic (10% Pd/C) hydrogenation of the double bond in the oxabicyclo[2.2.1]heptene fragment of substituted fused 1-oxo-3a,6-epoxyisoindoles is described. A continuous-flow hydrogenation device that incorporates in situ hydrogen generation by electrolysis of water was used. Changing the hydrogen source from water to deuterium oxide provides possibility to synthesize deuterated oxoepoxyisoindolones. Hydrogenation is stereoselective to give exclusively exo-cis deuterated derivatives.