Darzens reaction promoted by KF/alumina: A novel stereoselective method for rapid and efficient synthesis of trans-α,β-epoxy ketones

Synthetic Communications

Volumn 37, Issue 11, 2007, Pages 1825-1832

  Sharifi, Ali ^a   Salimi, Roghiyeh ^a   Mirzaei, Mojtaba ^a   Abaee, M Saeed ^a  

^a CHEMISTRY AND CHEMICAL ENGINEERING RESEARCH CENTER OF IRAN   (Iran)

Author keywords

, epoxy ketones; Darzens reaction; KF alumina; Solid phase synthesis

Indexed keywords

ALDEHYDE; ALUMINUM OXIDE; KETONE DERIVATIVE; PHENACYL CHLORIDE;

ARTICLE; DARZENS REACTION; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS;

EID: 34250380978     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701316292     Document Type: Article

References (34)

1. Lancaster, M. Green Chemistry: An Introductory Text; Royal Society of Chemistry; Cambridge: UK, 2002.
2. 3 mediated organic synthesis. Tetrahedron 2002, 58, 9301-9320.
3. Wong, W. C.; Wang, D.; Forray, C.; Vaysse, P. J. J.; Branchek, T. A.; Gluchowski, C. A convenient synthesis of 2-amino-2-oxazolines and their pharmacological evaluation at cloned human alpha-adrenergic receptors. Bioorg. Med. Chem. Lett. 1994, 4, 2317-2322.
4. Yadav, V. K.; Kapoor, K. K. KF adsorbed on alumina effectively promotes the epoxidation of electron deficient alkenes by anhydrous t-BuOOH. Tetrahedron 1996, 52, 3659-3668.
5. Yamawaki, J.; Ando, T. Potassium fluoride on alumina as base for crown ether synthesis. Chem. Lett. 1980, 533-536.
6. Yamawaki, J.; Ando, T.; Hanafusa, T. N-alkylation of amides and N-heterocycles with potassium fluoride on alumina. Chem. Lett. 1981, 1143-1146.
7. Polyak, F.; Dorofeeva, T.; Sturkovich, R.; Goldberg, Y. A novel route to N-alkylated derivatives of aziridine-2-carboxylic acid. An alternative synthesis of (S,S)-Bz-Azy-Val-OMe. Synth. Commun. 1991, 21, 239-248.
8. 2COCH=55CHPh: A facile route to fluorine-containing gamma-nitro ketones. Chin. Chem. Lett. 1997, 8, 665-668.
9. Kumar, H. M. S.; Reddy, B. V. S.; Reddy, E. J.; Yadav, J. S. Microwave-assisted eco-friendly synthesis of 2-alkylated hydroquinones in dry media. Green Chem. 1999, 1, 141-142.
10. Rao, A. K. S. B.; Rao, C. G.; Singh, B. B. Potassium fluoride on alumina - An efficient reagent for isomerization of N-(2-(alkyl arylsulfonyl)ethyl)-2- methyl-5-nitro-1H-imidazoles. Synth. Commun. 1991, 21, 443-448.
11. Berree, F.; Marchand, E.; Morel, G. Base mediated reactions in solid-liquid media - A 1,3-dipolar cycloaddition route to pyrolidines and pyrroles from imino chlorosulfides. Tetrahedron Lett. 1992, 33, 6155-6158.
12. Peschke, B.; Bundgaard, J. G.; Breinholt, J. Synthesis of amino alcohols on solid support via sulfonium-ion mediated Darzens reaction. Tetrahedron Lett. 2001, 42, 5127.
13. House, H. O. Modern Synthetic Reactions; Benjamin: Menlo Park, CA, 1972, p. 670.
14. Martin, S. F. Synthesis of aldehydes, ketones, and carboxylic-acids from lower carbonyl-compounds by C-C coupling reactions. Synthesis 1979, 633-665.
15. (a) Wang, Z. T.; Xu, L. W.; Xia, C. G.; Wang, H. Q. Efficient synthesis of α-β-epoxy carbonyl compounds in acetonitrile: Darzens condensation of aromatic aldehydes with ethyl chloroacetate. Helv. Chim. Acta 2004, 87, 1958-1962;
16. (b) Arai, S.; Suzuki, Y.; Tokumaro, K.; Shioiri, T. Diastereoselective Darzens reaction of α-chloroesters, amides and nitriles with aromatic aldehydes under phase-transfer catalyzed conditions. Tetrahedron Lett. 2002, 43, 833-836;
17. (c) Arai, S.; Shioiri, T. Catalytic asymmetric Darzens condensation under phasetransfer-catalyzed conditions. Tetrahedron Lett. 1998, 39, 2145-2148.
18. (a) Corey, E. J.; Choi, S. Highly enantioselective routes to Darzens and acetate aldol products from achiral aldehydes and t-butyl bromoacetate. Tetrahedron Lett. 1991, 32, 2857-2860;
19. (b) Aggarwal, V. K.; Hynd, G.; Picoul, W.; Vasse, J. L. Highly enantioselective Darzens reaction of a camphor-derived sulfonium amide to give glycidic amides and their application in synthesis. J. Am. Chem. Soc. 2002, 124, 9964-9965;
20. (c) Jacobsen, E. N.; Deng, L.; Furukawa, Y.; Martínez, L. E. Enantioselective catalytic epoxidation of cinnamate esters. Tetrahedron 1994, 50, 4323-4334.
21. (a) Tanaka, K.; Shiraishi, R. Darzens condensation reaction in water. Green Chem. 2001, 3, 135-136;
22. (b) Jayachandran, J. P.; Balakrishnan, T.; Wang, M. L. Phasetransfer-catalyzed Darzens condensation of chloroacetonitrile with cyclohexanone using aqueous sodium hydroxide and a new phase transfer catalyst. J. Mol. Catal. A: Chem. 2000, 152, 91-98.
23. Kimachi, T.; Kinoshita, H.; Kusaka, K.; Takeuchi, Y.; Aoe, M.; Ju-ichi, M. The highly trans-selective Darzens reaction via ammonium ylides. Synlett 2005, 842-844.
24. (a) Sano, S.; Miyamoto, M.; Mitani, T.; Nagao, Y. A novel and efficient Darzens reaction catalyzed by magnesium bromide. Heterocycles 2006, 68, 459-463;
25. (b) Hirashita, T.; Kinoshita, K.; Yamamura, H.; Kaweai, M.; Araki, S. A facile preparation of indium enolates and their Reformatsky- and Darzens-type reactions. J. Chem. Soc., Perkin Trans. 1, 2000, 825-828;
26. (c) Pridgen, L. N.; Abdel-Majid, A. F.; Lantos, I.; Shilcart, S.; Eggleston, D. S. Chelation control in metal-assisted aldol addition reactions of -halogenated imide enolates leading to predominantly anti stereoselectivity: An example of a stereocontrolled Darzens reaction. J. Org. Chem. 1993, 58, 5107-5117.
27. Yamawaki, J.; Kawate, T.; Ando, T.; Hanafusa, T. Potassium fluoride on alumina - An efficient solid base for elimination, addition, and condensation. Bull. Chem. Soc. Jpn. 1983, 56, 1885-1886.
28. (a) Sharifi, A.; Mirzaei, M.; Naimi-Jamal, M. R. Copper-catalysed oxidative homo-coupling of terminal acetylenes on alumina assisted by microwave irradiation. J. Chem. Res., Synop. 2002, 628-630;
29. (b) Sharifi, A.; Mojtahedi, M. M.; Saidi, M. R. Microwave irradiation techniques for the Cannizzaro reaction. Tetrahedron Lett. 1999, 40, 1179-1180;
30. (c) Sharifi, A.; Mirzaei, M.; Naimi-Jamal, M. R. Modified Glaser reaction of terminal alkynes on KF/alumina. Monatsh. Chem. 2006, 137, 213-217;
31. (d) Sharifi, A.; Mirzaei, M.; Naimi-Jamal, M. R. Mild and solvent-free alkynylation of ketones on the KF/alumina. Synth. Commun. 2005, 35, 1039-1044.
32. Lv, J.; Wang, X.; Liu, J.; Zhang, L.; Wang, Y. Catalytic asymmetric epoxidation of chalcones under poly(ethylene glycol)-supported Cinchona ammonium salt catalyzed conditions. Tetrahedron: Asymmetry 2006, 17, 330-335.
33. Bickley, J. F.; Gillmore, A. T.; Roberts, S. M.; Skidmore, J.; Steiner, A. Synthesis and reactions of some optically active epoxides formally derived from tertiary allylic alcohols. J. Chem. Soc., Perkin Trans. 2001, 1, 1109-1115.
34. Paquette, L. A. Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons: Chichester, 1995, Vol. 6, p. 4223.