Russian Chemical Bulletin

, Volume 64, Issue 1, pp 112–126

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

  • V. P. Zaytsev
  • F. I. Zubkov
  • D. F. Mertsalov
  • D. N. Orlova
  • E. A. Sorokina
  • E. V. Nikitina
  • A. V. Varlamov
Full Articles

DOI: 10.1007/s11172-015-0829-2

Cite this article as:
Zaytsev, V.P., Zubkov, F.I., Mertsalov, D.F. et al. Russ Chem Bull (2015) 64: 112. doi:10.1007/s11172-015-0829-2

Abstract

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.

Keywords

continuous-flow reactor heterogeneous catalytic hydrogenation reduction 3a,6-epoxyisoindoles deuteration 

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • V. P. Zaytsev
    • 1
    • 2
  • F. I. Zubkov
    • 1
  • D. F. Mertsalov
    • 1
  • D. N. Orlova
    • 1
  • E. A. Sorokina
    • 1
  • E. V. Nikitina
    • 1
  • A. V. Varlamov
    • 1
  1. 1.Deparment of Organic ChemistryPeople’s Friendship University of RussiaMoscowRussian Federation
  2. 2.Shared Research and Educational Center of Physico-Chemical Studies of New Materials, Substances, and Catalytic Systems”MoscowRussian Federation