Table of Contents
Organic Chemistry International
Volume 2013, Article ID 127585, 5 pages
http://dx.doi.org/10.1155/2013/127585
Research Article

Regioselective and Chemoselective Reduction of , -Unsaturated Carbonyl Compounds by /Ba as a Reducing System

Department of Chemistry, Faculty of Sciences, Mahabad Branch, Islamic Azad University, Mahabad 59135-443, Iran

Received 24 February 2013; Revised 12 April 2013; Accepted 12 April 2013

Academic Editor: Robert Salomon

Copyright © 2013 Mina Mohamadi et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. S. Varma and G. W. Kabalka, “Selective reduction of a, β-unsaturated nitrocompounds with sodium borohydride in methanolic solutions: a facile route to nitroalkenes,” Synthetic Communications, vol. 15, no. 2, pp. 151–155, 1985. View at Publisher · View at Google Scholar
  2. D. C. Sarkar, A. R. Das, and B. C. Ranu, “Use of zinc borohydride as an efficient and highly selective reducing agent. Selective reduction of ketones and conjugated aldehydes over conjugated enones,” Journal of Organic Chemistry, vol. 55, no. 22, pp. 5799–5801, 1990. View at Google Scholar · View at Scopus
  3. C. F. Nutaitis and J. E. Bernardo, “Regioselective 1,2-reduction of conjugated enones and enals with sodium monoacetoxyborohydride: preparation of allylic alcohols,” Journal of Organic Chemistry, vol. 54, no. 23, pp. 5629–5630, 1989. View at Google Scholar · View at Scopus
  4. S. Krishnamurthy and H. C. Brown, “9-borabicyclo[3.3.1]nonane as a highly selective reducing agent for the facile conversion of α,β-unsaturated aldehydes and ketones to the corresponding allylic alcohols in the presence of other functional groups,” Journal of Organic Chemistry, vol. 40, no. 12, pp. 1864–1865, 1975. View at Google Scholar · View at Scopus
  5. S. Krishnamurthy and H. C. Brown, “Selective reductions. 22. Facile reduction of α,β-unsaturated aldehydes and ketones with 9-borabicyclo[3.3.1]nonane. A remarkably convenient procedure for the selective conversion of conjugated aldehydes and ketones to the corresponding allylic alcohols in the presence of other functional groups,” Journal of Organic Chemistry, vol. 42, no. 7, pp. 1197–1201, 1977. View at Google Scholar · View at Scopus
  6. S. Kim, Y. C. Moon, and K. H. Ahn, “Lithium n-butylborohydride as a selective reducing agent for the reduction of enones, cyclic ketones, and selected carbonyl compounds,” Journal of Organic Chemistry, vol. 47, no. 17, pp. 3311–3315, 1982. View at Google Scholar · View at Scopus
  7. E. J. Corey, K. B. Becker, and R. K. Varma, “Efficient generation of the 15S configuration in prostaglandin synthesis. Attractive interactions in stereochemical control of carbonyl reduction,” Journal of the American Chemical Society, vol. 94, no. 24, pp. 8616–8618, 1972. View at Google Scholar · View at Scopus
  8. J. C. Fuller, E. L. Stangeland, C. T. Goralski, and B. Singaram, “Aminoborohydrides. 2. Regiospecific reductions of α,β-unsaturated carbonyl compounds with lithium pyrrolidinoborohydride. A facile conversion of α,β-unsaturated aldehydes and ketones to the corresponding allylic alcohols in high purity,” Tetrahedron Letters, vol. 34, no. 2, pp. 257–260, 1993. View at Publisher · View at Google Scholar · View at Scopus
  9. B. Ganem, “Conjugate reduction and reductive alkylation of α,β-unsaturated cyclohexenones using potassium tri-sec-butylborohydride,” Journal of Organic Chemistry, vol. 40, no. 1, pp. 146–147, 1975. View at Google Scholar · View at Scopus
  10. J. M. Fortunato and B. Ganem, “Lithium and potassium trialkylborohydrides. Reagents for direct reduction of α,β-unsaturated carbonyl compounds to synthetically versatile enolate anions,” Journal of Organic Chemistry, vol. 41, no. 12, pp. 2194–2200, 1976. View at Google Scholar · View at Scopus
  11. J. L. Luche, “Lanthanides in organic chemistry. 1. Selective 1,2 reductions of conjugated ketones,” Journal of the American Chemical Society, vol. 100, no. 7, pp. 2226–2227, 1978. View at Google Scholar · View at Scopus
  12. A. L. Gemal and J. L. Luche, “Lanthanoids in organic synthesis. 6. The reduction of α-enones by sodium borohydride in the presence of lanthanoid chlorides: synthetic and mechanistic aspects,” Journal of the American Chemical Society, vol. 103, no. 18, pp. 5454–5459, 1981. View at Google Scholar · View at Scopus
  13. H. Fujii, K. Oshima, and K. Utimoto, “A facile and selective 1,2-reduction of conjugated ketones with NaBH4 in the presence of CaCl2,” Chemistry Letters, vol. 20, no. 10, pp. 1847–1848, 1991. View at Publisher · View at Google Scholar
  14. H. Firouzabadi, M. Adibi, and M. Ghadami, “Modified borohydride agents, bis(triphenylphosphine) (tetra-hydroborato)zinc complex [Zn(BH4)2(PPh3)2] and (triphenylphosphine) (tetrahydroborato)zinc complex [Zn(BH4)2(PPh3)]. New ligand metal borohydrides as stable, efficient, and versatile reducing agents,” Phosphorus, Sulfur and Silicon and Related Elements, vol. 142, pp. 191–220, 1998. View at Google Scholar · View at Scopus
  15. H. Firouzabadi, M. Adibi, and B. Zeynizadeh, “Modified borohydride agents; efficient reduction of azides with (1,4-diazabicyclo[2.2.2]octane) (tetrahydroborato)zinc complex [Zn(BH4)2(dabco)] and methyltriphenylphosphonium tetrahydroborate [MePh3P+BH4  −],” Synthetic Communications, vol. 28, no. 7, pp. 1257–1273, 1998. View at Google Scholar · View at Scopus
  16. A. R. Sande, M. H. Jagadale, R. B. Mane, and M. M. Salunkhe, “Borohydride reducing agent derived from anion exchange resin: selective reduction of α, β-unsaturated carbonyl compounds,” Tetrahedron Letters, vol. 25, no. 32, pp. 3501–3504, 1984. View at Google Scholar · View at Scopus
  17. D. Setamdideh, B. Khezri, M. Rahmatollahzadeh, and A. Aliporamjad, “Mild and efficient reduction of organic carbonyl compounds to their corresponding alcohols with Zn(BH4)2 under protic condition,” Asian Journal of Chemistry, vol. 24, no. 8, pp. 3591–3596, 2012. View at Google Scholar
  18. D. Setamdideh and M. Rafig, “Reduction of carbonyl compounds to their corresponding alcohols by (nicotine)(tetrahydroborato)zinc complex as a new stable and efficient reducing agent,” E-Journal of Chemistry, vol. 9, no. 4, pp. 2338–2345, 2012. View at Publisher · View at Google Scholar
  19. D. Setamdideh and M. Rahmatollahzadeh, “Efficient and convenient reduction of organic carbonyl compounds to their corresponding alcohols by Zn(BH4)2/charcoal in THF,” Journal of the Mexican Chemical Society, vol. 56, no. 3, 2012. View at Google Scholar
  20. D. Setamdideh, B. Khezri, and M. Rahmatollahzadeh, “Zn(BH4)2/Al2O3: a new synthetic method for the efficient and convenient reduction of organic carbonyl compounds to their corresponding alcohols,” Journal of the Serbian Chemical Society, vol. 79, pp. 1–13, 2013. View at Google Scholar
  21. H. Firouazabadi and M. Adibi, “Modified borohydride agents 1a-d, methyltriphenylphosphonium tetrahydroborate; MePh3P+BH4  − as a selective and an efficient reducing agent,” Synthetic Communications, vol. 26, no. 13, pp. 2429–2441, 1996. View at Google Scholar · View at Scopus
  22. H. Firouzabadi and M. Adibi, “Methyltriphenylphosphonium tetrahydroborate (MePh3PBH4). A stable, selective and versatile reducing agent,” Phosphorus, Sulfur and Silicon and Related Elements, vol. 142, pp. 125–147, 1998. View at Google Scholar · View at Scopus
  23. R. O. Hutchins and D. Kandasamy, “Reductions of conjugated carbonyl compounds with cyanoborohydride in acidic media,” Journal of Organic Chemistry, vol. 40, no. 17, pp. 2530–2533, 1975. View at Google Scholar · View at Scopus
  24. K. S. Ravikumar, S. Baskaran, and S. Chandrasekaran, “Diisopropoxytitanium(III) tetrahydroborate: a highly useful reagent for the remarkably selective 1,2-reduction of α,β-unsaturated carbonyl compounds,” Journal of Organic Chemistry, vol. 58, no. 22, pp. 5981–5982, 1993. View at Google Scholar · View at Scopus
  25. D. Setamdideh and B. Zeynizadeh, “Mild and convenient method for reduction of carbonyl compounds with the NaBH4/charcoal system in wet THF,” Zeitschrift für Naturforschung B, vol. 61, no. 10, pp. 1275–1281, 2006. View at Google Scholar · View at Scopus
  26. B. Zeynizadeh and T. Behyar, “Fast and efficient method for reduction of carbonyl compounds with NaBH4/wet SiO2 under solvent free condition,” Journal of the Brazilian Chemical Society, vol. 16, no. 6A, pp. 1200–1209, 2005. View at Google Scholar · View at Scopus
  27. B. Zeynizadeh and F. Shirini, “Mild and efficient reduction of α,β-unsaturated carbonyl compounds, α-diketones and acyloins with sodium borohydride/Dowex1-x8 system,” Bulletin of the Korean Chemical Society, vol. 24, no. 3, pp. 295–298, 2003. View at Google Scholar · View at Scopus
  28. D. Setamdideh, B. Khezri, and A. Alipouramjad, “NaBH4/DOWEX(R)50WX4: a convenient reducing system for fast and efficient reduction ofcarbonyl compounds to their corresponding alcohols,” Journal of the Chinese Chemical Society, 2013. View at Publisher · View at Google Scholar