Skip to main content
SpringerLink
Log in

Asymmetric Hydrogenation of 3,4-Hexanedione over PtSn Catalysts

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

In this work, some results of the liquid-phase racemic and enantioselective hydrogenation of 3,4-hexanedione are presented. The catalysts employed were platinum-based, supported on SiO2. Monometallic catalysts were modified with organotin precursors either chiral (hexa(−)-menthylditin, Men3Sn–SnMen3) or achiral (tetrabutyltin, SnBu4), and they were obtained via surface organometallic chemistry on metals techniques. Asymmetric system was selective to 4-hydroxyhexan-3-one, the enantiomeric excess achieved being 17%.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

Notes

  1. In CDCl3; chemical shifts, δ, in ppm with respect to TMS; multiplicity, n°H, coupling constants nJ(Sn,H) in Hz, in parenthesis.

  2. In CDCl3; chemical shifts, δ, in ppm with respect to TMS; coupling constants n J(Sn,C) in Hz, in parentheses.

  3. In CDCl3; chemical shifts, δ, in ppm with respect to (CH3)4Sn.

References

  1. Zuo X, Liu H, Tian J (2000) J Mol Catal A 157:217

    Article  CAS  Google Scholar 

  2. Nieminen V, Taskinen A, Hotokka M, Murzin DY (2007) J Catal 245:228

    Article  CAS  Google Scholar 

  3. Blaser HU, Jalett HP, Mtiller M, Studer M (1997) Catal Today 37:441

    Article  CAS  Google Scholar 

  4. Sutyinszki M, Szöri K, Felflödi K, Bartók M (2002) Catal Commun 3:125

    Article  CAS  Google Scholar 

  5. Slipszenko J, Griffiths S, Johnston P, Simons K, Vermeer W, Wells P (1998) J Catal 179:267

    Article  CAS  Google Scholar 

  6. Sonderegger OJ, Bürgi T, Baiker A (2003) J Catal 215:116

    Article  CAS  Google Scholar 

  7. Toukoniitty E, Nieminen V, Taskinen A, Päivärinta J, Hotokka M, Murzin DY (2004) J Catal 224:326

    Article  CAS  Google Scholar 

  8. Toukoniitty E, Franceschini S, Vaccari A, Murzin DYu (2006) Appl Catal A 300:147

    Article  CAS  Google Scholar 

  9. Ruiz D, Claver C, Reyes P (2009) In: XVI Argentine congress on catalysis

  10. Basset JM et al (2009) In: Basset JM, Psaro R, Roberto D, Ugo R (eds) Modern surface organometallic chemistry. Wiley-VCH, Weinheim, chaps 1 and 2

  11. Vetere V, Faraoni MB, Santori GF, Podestá JC, Casella ML, Ferretti OA (2005) Catal Today 107:266

    Article  Google Scholar 

  12. Vetere V, Faraoni MB, Santori GF, Podestá JC, Casella ML, Ferretti OA (2004) J Catal 226:457

    Article  CAS  Google Scholar 

  13. Podestá JC, Radivoy GE (1994) Organometallics 13:3364

    Article  Google Scholar 

  14. Vetere V (2007) Ph.D. thesis, University of La Plata, Argentina

  15. Ferretti OA, Casella ML (2009) In: Basset J-M, Psaro R, Roberto D, Ugo R (eds) Modern surface organometallic chemistry. Wiley-VCH, Weinheim, chap 6

  16. Santori GF, Casella ML, Siri GJ, Adúriz HR, Ferretti OA (2000) Appl Catal A 197:141

    Article  CAS  Google Scholar 

  17. Boué S, Gielen M, Nasielski J, Lieutenant JP, Spielman R (1969) Bull Soc Chim Belges 78:135

    Google Scholar 

  18. Gielen M, Mokhtar-Jamaï H (1977) J Organomet Chem 129:325

    Article  CAS  Google Scholar 

  19. Jastrzebski JTBH, Wehman E, Boersma J, van Koten G (1991) J Organomet Chem 413:43

    Article  CAS  Google Scholar 

  20. van Koten G, Jastrzebski JTBH, Noltes JG, Pontenagel WMGF, Kroon J, Spek AL (1978) J Am Chem Soc 100:5021

    Article  Google Scholar 

  21. Schumann H, Wassermann BC, Pickardt J (1993) Organometallics 12:3051

    Article  CAS  Google Scholar 

  22. Lucas C, Santini C, Prinz M, Cordonnier MA, Basset JM, Connil MF, Jousseaume B (1996) J Organomet Chem 520:101

    Article  CAS  Google Scholar 

  23. Faraoni MB, Ayala AD, Vetere V, Casella ML, Ferretti OA, Podestá JC (2005) Appl Organomet Chem 19:465

    Article  CAS  Google Scholar 

  24. Radivoy GE (1997) Ph.D. thesis, University of South, Argentina

  25. Goguet A, Aouine M, Cadete Santos Aires FJ, de Mallmann A, Schweich D, Candy JP (2002) J Catal 209:135

    Article  CAS  Google Scholar 

  26. Schreier M, Regalbuto JR (2004) J Catal 225:190

    Article  CAS  Google Scholar 

  27. Ramallo López JM, Santori GF, Giovanetti L, Casella ML, Ferretti OA, Requejo FG (2003) J Phys Chem B 107:11441

    Article  Google Scholar 

  28. Baiker A (1997) J Mol Catal A 115:473

    Article  CAS  Google Scholar 

  29. Zhang J, Yan X, Liu H (2001) J Mol Catal A 176:281

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work has been sponsored by UNLP (Project X487, Argentina) and ANPCyT (PICT 14-11243, Argentina).

Author information

Authors and Affiliations

  1. CINDECA (CCT-La Plata, CONICET, UNLP), 47 no 257, 1900, La Plata, Argentina

    Virginia Vetere & Mónica L. Casella

  2. INQUISUR (CCT-Bahía Blanca, CONICET, UNS) (Miembro de la CIC), Av. Alem N. 1253, 8000, Bahía Blanca, Argentina

    María B. Faraoni & Julio C. Podestá

Authors
  1. Virginia Vetere
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. María B. Faraoni
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Julio C. Podestá
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mónica L. Casella
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mónica L. Casella.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vetere, V., Faraoni, M.B., Podestá, J.C. et al. Asymmetric Hydrogenation of 3,4-Hexanedione over PtSn Catalysts. Catal Lett 138, 34–39 (2010). https://doi.org/10.1007/s10562-010-0373-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-010-0373-5

Keywords

Search

Navigation