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Catalysis Letters

, Volume 117, Issue 3–4, pp 91–98 | Cite as

Hydrogenation of 1,2-indanedione over heterogeneous cinchonidine-modified platinum catalysts

  • Igor Busygin
  • Michael Rosenholm
  • Esa Toukoniitty
  • Dmitry Yu. MurzinEmail author
  • Reko LeinoEmail author
Article

Abstract

Hydrogenation of the prochiral diketone, 1,2-indanedione was for the first time investigated using cinchonidine-modified Pt/Al2O3 as a catalyst. The influence of the reaction parameters on catalyst activity, regio- and enantioselectivity was studied revealing fully regioselective hydrogenation of the C(2)-keto group. Enantioselectivities of the (R)- versus (S)-2-hydroxy-1-indanone varied from low to moderate in favor of the (R)-enantiomer.

Keywords

1,2-indanedione 2-hydroxy-1-indanone heterogeneous hydrogenation cinchonidine 

Graphical abstract

A systematic study of enantioselective hydrogenation of 1,2-indanedione – a new substrate for chirally modified heterogeneous catalysts – over cinchonidine modified Pt/Al2O3 is presented. The influence of the reaction parameters on activity, regio- and enantioselectivity was studied.

Notes

Acknowledgments

Financial support from the Academy of Finland (Project No. 201207) and the Graduate School of Bioorganic and Medicinal Chemistry is gratefully acknowledged.

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Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  1. 1.Laboratory of Organic ChemistryÅbo Akademi UniversityÅboFinland
  2. 2.Laboratory of Industrial ChemistryÅbo Akademi UniversityÅboFinland

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