An Efficient Catalyst for Aldol Condensation Reactions

Year 2017, Volume: 4 Issue: 2, 517 - 524, 28.03.2017

Yusuf Hassan Rosa Kleın Yusuf Hassan

https://doi.org/10.18596/jotcsa.293058

Cited By: 2

Abstract

A
New manganese complex was synthesised around S,S-1,2-diaminocyclohexane linked ketopinic acid scaffold, and
successfully utilised as catalyst in the aldol condensation reactions of
benzaldehyde with various aliphatic ketones to obtain  products with excellent yield of >99%.

Keywords

Lewis acid, ketopinic acid, catalysis

References

• 1. Heathcock CH, Ellis JE, McMurry JE, Coppolino A. Acid-catalyzed Robinson Annelations. Tetrahedron Letters. January 1971;12(52):4995–6.
• 2. Vashchenko V, Kutulya L, Krivoshey A. Simple and Effective Protocol for Claisen—Schmidt Condensation of Hindered Cyclic Ketones with Aromatic Aldehydes. ChemInform [Internet]. November 20, 2007 [source 03 April 2017];38(47).
• 3. Badía C, Castro JM, Linares-Palomino PJ, Salido S, Altarejos J, Nogueras M, vd. (E)-6-(2,2,3-Trimethyl-cyclopent-3-enyl)-hex-4-en-3-one. Molbank. March 29, 2004;2004(1):M388.
• 4. Sugiura M, Ashikari Y, Nakajima M. One-Pot Synthesis of β,β-Disubstituted α,β-Unsaturated Carbonyl Compounds. The Journal of Organic Chemistry. September 04, 2015;80(17):8830–5.
• 5. Wang Z, Yin G, Qin J, Gao M, Cao L, Wu A. An Efficient Method for the Selective Iodination of α,β-Unsaturated Ketones. Synthesis. November 2008;2008(22):3675–81.
• 6. Climent MJ, Corma A, Iborra S, Primo J. Base Catalysis for Fine Chemicals Production: Claisen-Schmidt Condensation on Zeolites and Hydrotalcites for the Production of Chalcones and Flavanones of Pharmaceutical Interest. Journal of Catalysis. January 1995;151(1):60–6.
• 7. Rao KK, Gravelle M, Valente JS, Figueras F. Activation of Mg–Al Hydrotalcite Catalysts for Aldol Condensation Reactions. Journal of Catalysis. January 1998;173(1):115–21.
• 8. Corma A. Alkaline-substituted sepiolites as a new type of strong base catalyst. Journal of Catalysis. July 1991;130(1):130–7.
• 9. Corma A, Fornés V, Martín-Aranda RM, García H, Primo J. Zeolites as base catalysts: Condensation of aldehydes with derivatives of malonic esters. Applied Catalysis. March 1990;59(1):237–48.
• 10. Climent M. Increasing the basicity and catalytic activity of hydrotalcites by different synthesis procedures. Journal of Catalysis. July 2004;225(2):316–26.
• 11. Yang K-S, Lee W-D, Pan J-F, Chen K. Chiral Lewis Acid-Catalyzed Asymmetric Baylis−Hillman Reactions. The Journal of Organic Chemistry. February 2003;68(3):915–9.
• 12. Kureshy RI, Khan NH, Abdi SHR, Iyer P, Bhatt AK. Enantioselective catalytic epoxidation of nonfunctionalized prochiral olefins by dissymmetric chiral Schiff base complexes of Mn(III) and Ru(III) metal ions II. Journal of Molecular Catalysis A: Chemical. June 1997;120(1–3):101–8.
• 13. Yoshikawa N, Yamada YMA, Das J, Sasai H, Shibasaki M. Direct Catalytic Asymmetric Aldol Reaction. Journal of the American Chemical Society. May 1999;121(17):4168–78.