Simple and fast microwave-assisted ruthenium_catalyzed direct aldol reaction


Elahe Keshavarz, Khalil Tabatabaeian, Manouchehr Mamaghani and Nosrat O. Mahmoodi


A microwave-assisted method was developed for the synthesis of aldol adducts using RuCl3.nH2O-BINAP as an efficient catalyst. Important advantages of this technology include environmentally benign condition, highly accelerated rate of the reaction with an improvement in the chemoselectivity and quality of the products.


DOI: j.ccl.2012.4.001

Keywords: Aldol reaction ,Catalyst ,Microwave technique

How to cite this paper:

Keshavarz, E., Tabatabaeian, K., Mamaghani, M & Mahmoodi, N. (2012). Simple and fast microwave-assisted ruthenium_catalyzed direct aldol reaction.Current Chemistry Letters, 1(2), 91-94.


References

Tabatabaeian K., Heidari H., Mamaghani M., Mahmoodi N. O. (2012) Ru(II) Complexes Bearing Tertiary Phosphine Ligands: A Novel and Efficient Homogeneous Catalyst for One-pot Synthesis of Dihydropyrano [3,2-] Chromene and Tetrahydrobenzo [] pyran Derivatives. Appl. Organomet. Chem., 26(2), 56-61.

Delas C., Moïse C. (2000) A Combination of Allyltitanation and Tandem Aldol-Tischtschenko Reactions using Tetraisopropoxytitanium. Synthesis, 2, 251-254.

Geary L. M., Hultin P. G. (2009) The State of the Art in Asymmetric Induction: the Aldol Reaction as a Case study. Tetrahedron: Asymmetry, 20(2), 131-173.

Chaskar A. (2012) Phosphomolybdic Acid Accelerated One-pot Synthesis of 1-Aryl-1H, 3H-thiazolo[3, 4-a]benzimidazoles. Curr. Chem. Lett., 1(1), 21-26.

Miura T., Ina M., Imai K., Nakashima K., Masuda A., Tada N., Imai N., Itoh A. (2011) β-Aminosulfonamide-catalyzed Direct Asymmetric Aldol Reaction in Brine. Synlett, 3, 410-415.

Chandrasekhar S., Johny K., Reddy C. R. (2009) Proline-threonine Dipeptide as an Organocatalyst for the Direct Asymmetric Aldol Reaction. Tetrahedron: Asymmetry, 20(15), 1742-1745.

Rani R., Peddinti R. K. (2010) Camphor-10-sulfonamide-based Prolinamide Organocatalyst for the Direct Intermolecular Aldol Reaction between Ketones and Aromatic Aldehydes. Tetrahedron: Asymmetry, 21(7), 775-779

Chen F., Huang S., Zhang H., Liu F., Peng Y. (2008) Proline-based Dipeptides with two Amide units as Organocatalyst for the Asymmetric Aldol Reaction of Cyclohexanone with Aldehydes. Tetrahedron, 64(40), 9585-9591.

Siyutkin D. E., Kucherenko A. S., Zlotin S. G. (2009) Hydroxy-α-amino Acids Modified by Ionic Liquid Moieties: Recoverable Organocatalysts for Asymmetric Aldol Reactions in the Presence of Water. Tetrahedron, 65(7), 1366-1372.

Tzeng Z.-H., Chen H.-Y., Reddy R. J., Huang C.-T., Chen K. (2009) Highly Diastereo- and Enantioselective Direct Aldol Reactions Promoted by Water-compatible Organocatalysts Bearing a Pyrrolidinyl-camphor Structural Scaffold. Tetrahedron, 65(15), 2879-2888.

Masters C. (1981) Homogeneous Transition Metal Catalysis-a gentle Art, Chapman and Hall Ltd.

Meijere A. D., Diederich F. Metal-catalyzed Cross-coupling Reactions, Vol. 2, 2nd edn. Wiely-VCH, New York.

Dou X.-Y., Wang J.-Q., Du Y., Wang E., He L.-N. (2007). Guanidinium Salt Functionalized PEG: An Effective and Recyclable Homogeneous Catalyst for the Synthesis of Cyclic Carbonates from CO2 and Epoxides under Solvent-free Conditions. Synlett, 19, 3058-3062.

Murahashi S.-I. (2004) Ruthenium in Organic Synthesis, Wiely-VCH: New York.

Murai S. (1999) Activation of Unreactive Bonds and Organic Synthesis, Springer.

Tabatabaeian K., Mamaghani M., Mahmoodi N. O., Keshavarz E. (2010) Facile Access to Aldol Products from Aromatic and Heteroaromatic Aldehydes using Ruthenium Catalyst. Int. J. Inorg. Chem., ID 621376, 4 pages.

Tabatabaeian K., Keshavarz E., Mamaghani M., Mahmoodi N. O. (2010) An Efficient RuIII/BINAP Catalytic System for the Aldol Reactions of Ketones with Various Aldehydes. Arkivoc IX, 155-162.

Tabatabaeian K., Keshavarz E., Mamaghani M., Mahmoodi N. O. (2011) RuCl3.nH2O as Catalyst for Diastereoselective Direct Aldol Reaction: An Efficient Route to Hormone Steroid Derivatives. Org. Chem. Int., ID, 325291, 5 pages.

Tabatabaeian K., Mamaghani M., Mahmoodi N. O., Keshavarz E. (2009) Ruthenium-catalyzed Cross Aldol Reaction with Aldehydes and Ketones. Arkivoc II, 68-75.

Wei H.-X., Jasoni R. L., Shao H., Hu J., Pare P. W. (2004) Anti-Selective and Regioselective Aldol Addition of Ketones with Aldehydes using MgI2 as Promoter. Tetrahedron, 60(51), 11829-11835.

Inoue H., Kikuchi M., Ito J.-I., Nishiyama H. (2008) Chiral Phebox-rhodium Complexes as Catalysts for Asymmetric Direct Aldol Reaction. Tetrahedron, 64(3), 493-499.

Keshavarz E., Tabatabaeian K., Mamaghani M., Mahmoodi N. O. (2011) Simple and Fast Ruthenium Catalyzed Direct Aldol Reaction: Scope and Limitations. 15th International Electronic Conference on Synthetic Organic Chemistry, (ECSOC-15).