How to cite this paper
Uma, R. (2012). Cesium carbonate mediated exclusive dialkylation of active methylene compounds.Current Chemistry Letters, 1(3), 123-132.
Refrences
1. Wolfe, J. P., Buchwald, S. L. (1997) improved functional group compatibility in the palladium-catalyzed amination of aryl bromides. Tetrahedron Lett. 38, 6359.
2. Cuny, G. D. (2003) Intramolecular ortho-arylation of phenols utilized in the synthesis of the aporphine alkaloids (±)-lirinidine and (±)-nuciferine. Tetrahedron Lett. 44, 8149.
3. (a) Parrish, J. P., Dueno, E. E., Kim, S., Jung, K. W. (2000) Improved Cs2CO3 promoted O-alkylation of acids. Synth. Commun., 30(15), 2687. (b) Dueno, E. E., Chu, F., Kim, S., Jung, K. W. (1999) "Cesium promoted O-alkylation of alcohols for the efficient ether synthesis" Tetrahedron Lett., 40, 1843.
4. Butler, J., Kellogg, R. M. (1981) Synthesis of sulfur-containing macrocycles using cesium thiolates. J. Org. Chem., 46, 4481.
5. Lavallée, J. F., Berthiaume, G., Deslongchamps, P., Grein, F. (1986) Intramolecular Michael addition of cyclic B-ketoester on conjugated acetylenic ketone. Tetrahedron Lett., 27, 5455.
6. Kumaraswamy, G., Pitchaiah, A., Ramakrishna, G., Ramakrishna, D. S., Sadaiah, K. (2006) Di-?-hydroxy-bis (N,N,N?,N?-tetramethylenediamine)-copper(II)chloride[Cu(OH)•TMEDA]2Cl2: an efficient, practical catalyst for benzylation and allylation of amides. Tetrahedron Lett., 47, 2013.
7. Vogtle, F., Kissener, W. (1984) Cesium effect in C-C-bond forming reactions yielding large hydrocarbon rings. Chem. Ber.-Recueil, 117, 2538.
8. Dijkstra, G., Kruizinga, W. H., Kellogg, R. M. (1987) An assessment of the causes of the cesium effect. J. Org. Chem., 52, 4230.
9. Blum, Z. (1989) The cesium effect revisited, Acta Chemica Scandinavica, 43, 248.
10. Ostrowicki, A., Koepp, E., Vogtle, F. (1992) The cesium effect - syntheses of mediocyclic and macrocyclic-compounds. Top. Curr. Chem., 161, 37.
11. Flessner, T., Doye, S. (1999) "Cesium carbonate: "a powerful inorganic base in organic synthesis," J. Prak. Chem., 341, 186.
12. Salvatore, R. N.: Nagle, A. S.: Jung, K. W. (2002) Cesium effect: high chemoselectivity in direct N-alkylation of amines. J. Org. Chem., 67, 674.
13. Suk, Y., Shibasaki, M. (1998) The asymmetric synthesis of cyclopentane derivatives by palladium-catalyzed coupling of prochiral alkylboron compounds .Tetrahedron Asymmetry, 9, 3751.
14. Vaughan, W. S., Gu, H. H., McDaniel, K. F. (1997) Reaction of tetracarbonyl (?-allyl) manganese with carbon nucleophiles. Tetrahedron Lett., 38, 1885.
15. Laurenti, D., Feuerstein, M., Pepe, G., Doucet, H., Santelli, M. (2001) a new tetratertiary phosphine ligand and its use in Pd-catalyzed allylic substitution. J. Org. Chem., 66, 1633.
16. Kinoshita, H., Shinokubo, H., Oshima, k. (2004) water enables direct use of allyl alcohol for Tsuji?Trost reaction without activators. Org. Lett., 6, 4085.
17. King, J. F., Rathore, R., Lam, J. Y. L., Guo, Z. R., Klassen, D. F. (1992) PH optimization of nucleophilic reactions in water. J. Am. Chem. Soc., 114, 3028.
18. Yamamoto, Y., Nakagai, Y., Itoh, K. (2004) Ruthenium-catalyzed one-pot double allylation /cycloisomerization of 1, 3-dicarbonyl compounds leading to exo-methylene cyclopentanes. Chem. Eur. J., 10, 231.
19. Kimura, M., Mukai, R., Tanigawa, N., Tanaka, S., Tamaru, Y. (2003) Triethylborane as an efficient promoter for palladium-catalyzed allylation of active methylene compounds with allyl alcohols. Tetrahedron, 39, 7767.
20. Curran, D. P., Seong, C. M. (1992) Radical annulation reactions of allyl iodomalononitriles. Tetrahedron, 48, 2175.
21. Diezbarra, E.: Delahoz, A., Moreno, A., Sanchezverdu, P. (1991) Phase transfer catalysis without solvent: selective mono- or di-alkylation of malononitrile. J. Chem. Soc. Perkin Trans., 1, 2589.
22. Muthusamy, S., Srinivasan, P. (2005) Facile chemoselective rhodium carbenoid of active methylene compounds. Tetrahedron Lett., 46, 635.
23. Reynolds, R. C., Trask, T. W., Sedwick, W. D. (1991) 2,4-Dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine: a potential synthon for 5-(1-o-carboranylmethyl)pyrimidines. J. Org. Chem., 56, 2391.
24. Bhar, S., Chaudhuri, S. K., Sahu, S.G., Panja, C. (2001) Solvent-free synthesis of 4,4-bis-functionalized-1,6-dienes and 1,6-diynes on the surface of neutral alumina. Tetrahedron, 57, 9011.
25. Diez-Barra, E., De la Hoz, A., Moreno,A., Sanchez-Verdu, P. (1991) Phase transfer catalysis without solvent: selective mono- or di-alkylation of malononitrile. J. Chem. Soc. Perkin Trans., 1, 2589.
26. Shawn, R, H., Françoise, P., Van, A, M., Kim, F, A. (1990) Efficient synthesis of ?-(hydroxymethyl) ketones not available through aldol-type processes. Synthesis, 11, 1059.
27. Marquet, J., Moreno-Manas, M., Pacheco, P., Prat, M., Katritzky. A. R., Brycki, B. (1990) C-alkylation of B diketones with benzylpyridinium salts. Evidence for chain radical mechanisms, Tetrahedron, 46, 5333.
28. Yoshihara, N., Kitagawa, T., Ihara, I., Hasegawa, S., Hasegawa, T. (1992) Selective ?-Mono- and ?,?-Dialkylations of 1,3-Diketones Using Solid Base Prepared from Sodium Ethoxide and Alumina. Bull. Chem. Soc. Jpn., 65, 1185.
29. Ridvan, L., Z?vada, J. (1997) Mono-vs.dialkylation of carbanions. Effects of absolute and relative acidity of the conjugate carbon acids in selectivity control. Tetrahedron, 53, 14793.
30. Ranu, B. C., Banerjee, S., Jana, R. (2007) Ionic liquid as catalyst and solvent: the remarkable effect of a basic ionic liquid, [bmIm]OH on Michael addition and alkylation of active methylene compounds. Tetrahedron, 63, 776.
31. Rolin.y., Gebehenne.C., Derien. S., Dunach. E., Perichon. J. (1993) Electrochemical activation of zinc in the coupling reaction of ?-bromoesters with carbonyl compounds. J. Organomet. Chem., 461, 9.
32. Fotouhi, N., Joshi, P., Fry, D., Cook, C., Tilley, J. W., Kaplan, G., Hanglow, A., Rowan, K.., Schwinge, V., Wolitzky, B., (2000) The design and synthesis of potent cyclic peptide VCAM–VLA-4 antagonists incorporating an achiral Asp-Pro mimetic. Bioorg. Med. Chem. Let, 10, 1171.
33. Baumstark, A. L., Vasquez, P. C., Chen, Y. X. (1994) Synthesis and thermolysis of ketal derivatives of 3-hydroxy-1, 2-dioxolanes . J. Org. Chem., 59, 6692.
2. Cuny, G. D. (2003) Intramolecular ortho-arylation of phenols utilized in the synthesis of the aporphine alkaloids (±)-lirinidine and (±)-nuciferine. Tetrahedron Lett. 44, 8149.
3. (a) Parrish, J. P., Dueno, E. E., Kim, S., Jung, K. W. (2000) Improved Cs2CO3 promoted O-alkylation of acids. Synth. Commun., 30(15), 2687. (b) Dueno, E. E., Chu, F., Kim, S., Jung, K. W. (1999) "Cesium promoted O-alkylation of alcohols for the efficient ether synthesis" Tetrahedron Lett., 40, 1843.
4. Butler, J., Kellogg, R. M. (1981) Synthesis of sulfur-containing macrocycles using cesium thiolates. J. Org. Chem., 46, 4481.
5. Lavallée, J. F., Berthiaume, G., Deslongchamps, P., Grein, F. (1986) Intramolecular Michael addition of cyclic B-ketoester on conjugated acetylenic ketone. Tetrahedron Lett., 27, 5455.
6. Kumaraswamy, G., Pitchaiah, A., Ramakrishna, G., Ramakrishna, D. S., Sadaiah, K. (2006) Di-?-hydroxy-bis (N,N,N?,N?-tetramethylenediamine)-copper(II)chloride[Cu(OH)•TMEDA]2Cl2: an efficient, practical catalyst for benzylation and allylation of amides. Tetrahedron Lett., 47, 2013.
7. Vogtle, F., Kissener, W. (1984) Cesium effect in C-C-bond forming reactions yielding large hydrocarbon rings. Chem. Ber.-Recueil, 117, 2538.
8. Dijkstra, G., Kruizinga, W. H., Kellogg, R. M. (1987) An assessment of the causes of the cesium effect. J. Org. Chem., 52, 4230.
9. Blum, Z. (1989) The cesium effect revisited, Acta Chemica Scandinavica, 43, 248.
10. Ostrowicki, A., Koepp, E., Vogtle, F. (1992) The cesium effect - syntheses of mediocyclic and macrocyclic-compounds. Top. Curr. Chem., 161, 37.
11. Flessner, T., Doye, S. (1999) "Cesium carbonate: "a powerful inorganic base in organic synthesis," J. Prak. Chem., 341, 186.
12. Salvatore, R. N.: Nagle, A. S.: Jung, K. W. (2002) Cesium effect: high chemoselectivity in direct N-alkylation of amines. J. Org. Chem., 67, 674.
13. Suk, Y., Shibasaki, M. (1998) The asymmetric synthesis of cyclopentane derivatives by palladium-catalyzed coupling of prochiral alkylboron compounds .Tetrahedron Asymmetry, 9, 3751.
14. Vaughan, W. S., Gu, H. H., McDaniel, K. F. (1997) Reaction of tetracarbonyl (?-allyl) manganese with carbon nucleophiles. Tetrahedron Lett., 38, 1885.
15. Laurenti, D., Feuerstein, M., Pepe, G., Doucet, H., Santelli, M. (2001) a new tetratertiary phosphine ligand and its use in Pd-catalyzed allylic substitution. J. Org. Chem., 66, 1633.
16. Kinoshita, H., Shinokubo, H., Oshima, k. (2004) water enables direct use of allyl alcohol for Tsuji?Trost reaction without activators. Org. Lett., 6, 4085.
17. King, J. F., Rathore, R., Lam, J. Y. L., Guo, Z. R., Klassen, D. F. (1992) PH optimization of nucleophilic reactions in water. J. Am. Chem. Soc., 114, 3028.
18. Yamamoto, Y., Nakagai, Y., Itoh, K. (2004) Ruthenium-catalyzed one-pot double allylation /cycloisomerization of 1, 3-dicarbonyl compounds leading to exo-methylene cyclopentanes. Chem. Eur. J., 10, 231.
19. Kimura, M., Mukai, R., Tanigawa, N., Tanaka, S., Tamaru, Y. (2003) Triethylborane as an efficient promoter for palladium-catalyzed allylation of active methylene compounds with allyl alcohols. Tetrahedron, 39, 7767.
20. Curran, D. P., Seong, C. M. (1992) Radical annulation reactions of allyl iodomalononitriles. Tetrahedron, 48, 2175.
21. Diezbarra, E.: Delahoz, A., Moreno, A., Sanchezverdu, P. (1991) Phase transfer catalysis without solvent: selective mono- or di-alkylation of malononitrile. J. Chem. Soc. Perkin Trans., 1, 2589.
22. Muthusamy, S., Srinivasan, P. (2005) Facile chemoselective rhodium carbenoid of active methylene compounds. Tetrahedron Lett., 46, 635.
23. Reynolds, R. C., Trask, T. W., Sedwick, W. D. (1991) 2,4-Dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine: a potential synthon for 5-(1-o-carboranylmethyl)pyrimidines. J. Org. Chem., 56, 2391.
24. Bhar, S., Chaudhuri, S. K., Sahu, S.G., Panja, C. (2001) Solvent-free synthesis of 4,4-bis-functionalized-1,6-dienes and 1,6-diynes on the surface of neutral alumina. Tetrahedron, 57, 9011.
25. Diez-Barra, E., De la Hoz, A., Moreno,A., Sanchez-Verdu, P. (1991) Phase transfer catalysis without solvent: selective mono- or di-alkylation of malononitrile. J. Chem. Soc. Perkin Trans., 1, 2589.
26. Shawn, R, H., Françoise, P., Van, A, M., Kim, F, A. (1990) Efficient synthesis of ?-(hydroxymethyl) ketones not available through aldol-type processes. Synthesis, 11, 1059.
27. Marquet, J., Moreno-Manas, M., Pacheco, P., Prat, M., Katritzky. A. R., Brycki, B. (1990) C-alkylation of B diketones with benzylpyridinium salts. Evidence for chain radical mechanisms, Tetrahedron, 46, 5333.
28. Yoshihara, N., Kitagawa, T., Ihara, I., Hasegawa, S., Hasegawa, T. (1992) Selective ?-Mono- and ?,?-Dialkylations of 1,3-Diketones Using Solid Base Prepared from Sodium Ethoxide and Alumina. Bull. Chem. Soc. Jpn., 65, 1185.
29. Ridvan, L., Z?vada, J. (1997) Mono-vs.dialkylation of carbanions. Effects of absolute and relative acidity of the conjugate carbon acids in selectivity control. Tetrahedron, 53, 14793.
30. Ranu, B. C., Banerjee, S., Jana, R. (2007) Ionic liquid as catalyst and solvent: the remarkable effect of a basic ionic liquid, [bmIm]OH on Michael addition and alkylation of active methylene compounds. Tetrahedron, 63, 776.
31. Rolin.y., Gebehenne.C., Derien. S., Dunach. E., Perichon. J. (1993) Electrochemical activation of zinc in the coupling reaction of ?-bromoesters with carbonyl compounds. J. Organomet. Chem., 461, 9.
32. Fotouhi, N., Joshi, P., Fry, D., Cook, C., Tilley, J. W., Kaplan, G., Hanglow, A., Rowan, K.., Schwinge, V., Wolitzky, B., (2000) The design and synthesis of potent cyclic peptide VCAM–VLA-4 antagonists incorporating an achiral Asp-Pro mimetic. Bioorg. Med. Chem. Let, 10, 1171.
33. Baumstark, A. L., Vasquez, P. C., Chen, Y. X. (1994) Synthesis and thermolysis of ketal derivatives of 3-hydroxy-1, 2-dioxolanes . J. Org. Chem., 59, 6692.