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

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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.

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.

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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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Authors and Affiliations

  1. Laboratory of Organic Chemistry, Åbo Akademi University, Åbo, Finland

    Igor Busygin, Michael Rosenholm & Reko Leino

  2. Laboratory of Industrial Chemistry, Åbo Akademi University, Åbo, Finland

    Esa Toukoniitty & Dmitry Yu. Murzin

Authors
  1. Igor Busygin
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  2. Michael Rosenholm
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  3. Esa Toukoniitty
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  4. Dmitry Yu. Murzin
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  5. Reko Leino
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Correspondence to Dmitry Yu. Murzin or Reko Leino.

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Busygin, I., Rosenholm, M., Toukoniitty, E. et al. Hydrogenation of 1,2-indanedione over heterogeneous cinchonidine-modified platinum catalysts. Catal Lett 117, 91–98 (2007). https://doi.org/10.1007/s10562-007-9123-8

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  • DOI: https://doi.org/10.1007/s10562-007-9123-8

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