Continuous-flow catalytic hydrogenation of 3a,6-epoxyisoindoles

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...

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Bibliographic Details
Published in:Russian chemical bulletin 2015-01, Vol.64 (1), p.112-126
Main Authors: Zaytsev, V. P., Zubkov, F. I., Mertsalov, D. F., Orlova, D. N., Sorokina, E. A., Nikitina, E. V., Varlamov, A. V.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Inorganic Chemistry
Organic Chemistry
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Summary: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.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-015-0829-2