Optimized Methodologies in Asymmetric Organic Synthesis Applying Microwaves
DOI:
https://doi.org/10.29356/jmcs.v53i3.998Keywords:
Microwaves, Reaction Optimization, Organocatalysts, β-amino Acids, β-peptidesAbstract
The use of microwave heating is a valuable tool for synthetic chemists. Being able to reduce reaction times and to increase product yield, this methodology offers to organic chemists the potential to optimize reaction processes. Additionally, microwave-assisted reactions provide more environmentally friendly reaction conditions. In this report, we describe results in the optimization of several organic reactions employed in the synthesis of various chiral molecules such as heterocycles, β-amino acids, and β-peptides, among others.
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References
1. Hayes, B. L. Microwave Synthesis, Chemistry at the Speed of Light. CEM Publishing. Matthews, NC: 2002.
2. Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett. 1986, 27, 279-282.
3. Giguere, R. J.; Bray, T. L.; Duncan, S. M.; Majetich, G. Tetrahedron Lett. 1986, 27, 4945-4948.
4. Kappe, C. O.; Dallinger, D. Nature Reviews Drug Discovery 2006, 5, 51-63.
5. a) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105; b) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717-727; c) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250-6284; d) de la Hoz, A.; Díaz-Ortiz, A.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164-178; e) Collins, J. M.; Leadbeater, N. E. Org. Biomol. Chem. 2007, 5, 1141-1150; f) Dallinger, D.; Kappe, O. Chem. Rev. 2007, 107, 2563-2591; g) Appukkuttan, P.; Van der Eycken, E. Eur. J. Org. Chem. 2008, 1133-1155; h) Polshettiwar, V.; Varma, R. S. Acc. Chem. Res. 2008, 41, 629-639; i) Polshettiwar, V.; Varma, R. S. Chem. Soc. Rev. 2008, 37, 1546-1557.
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14. Melgar-Fernández, R.; González-Olvera, R.; Olivares-Romero, J. L.; González-López, V.; Romero-Ponce, L.; Ramírez-Zárate, M. R.; Demare, P.; Regla, I.; Juaristi, E. Eur. J. Org. Chem. 2008, 655-672.
15. a) Portoghese, P. S.; Mikhail, A. A. J. Org. Chem. 1966, 31, 10591062; b) Braish, T. F.; Fox, D. E. J. Org. Chem. 1990, 55, 16841687.
16. a) Hoppe, D.; Hense, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316; b) Schütz, T. Synlett 2003, 901-902.
17. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360-416.
18. González-Olvera, R.; Demare, P.; Regla, I.; Juaristi, E. ARKIVOC 2008, 6, 61-72.
19. Stadler, A.; Kappe, C. O. J. Chem. Soc. Perkin Trans. 2 2000, 1363-1368.
20. a) Asami, M.; Sato, S.; Watanabe, H. Chem. Lett. 2000, 990-991; b) Sato, S.; Watanabe, H.; Asami, M. Tetrahedron: Asymmetry 2000, 11, 4329-4340; c) Basavaiah, D.; Rao, K. V.; Reddy, B. S. Tetrahedron: Asymmetry 2006, 17, 1041-1044; d) Basavaiah, D.; Rao, K. V.; Reddy, B. S. Tetrahedron: Asymmetry 2007, 18, 968974.
21. Olivares-Romero, J. L.; Juaristi, E. Tetrahedron 2008, 64, 99929998.
22. See for example: Kappe, C. O. Microwaves in Organic and Medicinal Chemistry. Wiley-VCH, Weinheim: 2005.
23. a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553; b) Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861-2863.
24. See for example: Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138-5175.
25. Ficken, G. E. US Patent 3,153,654. 1964.
26. Luppi, G.; Cozzi, P. G.; Monari, M.; Kaptein, B.; Broxterman, Q. B.; Tomasini, C. J. Org. Chem. 2005, 70, 7418-7421.
27. Kimura, S. Org. Biomol. Chem. 2008, 6, 1143-1148.
28. Juaristi, E.; Aviña, J. Pure Appl. Chem. 2005, 77, 1235-1241.
29. a) Klein, S.; Czekaj, M.; Molino, B.; Chu, V. Bioorg. Med. Chem. Lett. 1997, 7, 1773-1778; b) Cardillo, G.; Gentilucci, L.; Melchiorre, P.; Spampinato, S. Bioorg. Med. Chem. Lett. 2000, 10, 2755-2758; c) Sagan, S.; Milcent, T.; Ponsinet, R.; Convert, O.; Tasseau, O.; Chassaing, G.; Lavielle, S.; Lequin, O. Eur. J. Biochem. 2003, 270, 939-949; d) Szeto, H. H.; Schiller, P. W.; Zhao, K.; Luo, G. FASEB Journal 2004, 19, 118-120; e) Lind, R.; Greenhow, D.; Perry, S.; Kimmerlin, T.; Seebach, D. Chem. & Biodiversity 2004, 1, 1391-1400; f) Seebach, D.; Rueping, M.; Ardvidsson, P. I.; Kimmerlin, T.; Micuch, P.; Noti, C.; Langenegger, D.; Hoyer, D. Helv. Chim. Acta 2001, 84, 35033510; g) Epand, R. F.; Schmitt, M. A.; Gellman, S. H.; Sen, A.; Auger, M.; Hughes, D. W.; Epand, R. M. Mol. Membrane Biol. 2005, 22, 457-469; h) Mollica, A.; Paradisi, M. P.; Torino, D.; Spisani, S.; Lucente, G. Amino Acids 2006, 30, 453-459.
30. See for example: a) Reyes-Rangel, G.; Jiménez-González, E.; Olivares-Romero, J. L.; Juaristi, E. Tetrahedron: Asymmetry 2008, 19, 2839-2849; b) Ávila-Ortiz, C. G.; Reyes-Rangel, G.; Juaristi, E. Tetrahedron 2005, 61, 8372-8381; c) Castellanos, E.; Reyes-Rangel, G.; Juaristi, E. Helv. Chim. Acta 2004, 87, 10161024; d) Gutiérrez-García, V. M.; Reyes-Rangel, G.; MuñozMuñiz, O.; Juaristi, E. Helv. Chim. Acta 2002, 85, 4189-4199; e) Gutiérrez-García, V. M.; López-Ruiz, H.; Reyes-Rangel, G.; Juaristi, E. Tetrahedron 2001, 57, 6487-6496; f) Juaristi, E.; Balderas, M.; López-Ruiz, H.; Jiménez-Pérez, V. M.; KaiserCarril, M. L.; Ramírez-Quiros, Y. Tetrahedron: Asymmetry 1999, 10, 3493-3505.
31. Escalante, J.; González-Tototzin, M. A.; Aviña, J.; Muñoz-Muñiz, O.; Juaristi, E. Tetrahedron 2001, 57, 1883-1890.
32. Crystal data for 19: C22H26N2O2, monoclinic, space group P 2(1), a = 10.9924(11)Å, b = 6.5469(19)Å, c = 13.2954(09)Å, α = γ = 90°, β = 96.4848(68)°, V = 950.6Å3, crystal size: 0.3 × 0.2 × 0.1 mm3, R1 = 0.0441 (wR2 = 0.1087). Crystal data for 21: C22H26N2S2, monoclinic, space group P 2(1), a = 12.56660(50)Å, b = 6.03300(20)Å, c = 13.00150(59)Å, α = γ = 90°, β = 92.3405(15)°, V = 984.8776(68)Å3, crystal size: 0.88x0.20x0.15 mm3, R1 = 0.0427 (wR2 = 0.1223). Crystal data for 29: C23H23NO2, monoclinic, space group P 2(1), a = 9.8525(20)Å, b = 6.0365(12)Å, c = 16.2635(33)Å, α = γ = 90°, β = 104.788(30)°, V = 935.225Å3, crystal size: 0.3 × 0.2 × 0.1 mm3, R1 = 0.0379 (wR2 = 0.0932). CCDC 740273 (19), CCDC 740274 (21), and CCDC 740275 (29) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via http://www.ccdc.cam.ac.uk/data_request/cif.
33. Guzmán-Mejía, R.; Reyes-Rangel, G.; Juaristi, E. Nature Protocols 2007, 2, 2759-2766.
34. Díaz-Sánchez, B.; Iglesias-Arteaga, M.; Melgar-Fernández, R.; Juaristi, E. J. Org. Chem. 2007, 72, 4822-4825.
35. Wessjohann, L.; Mcgaffin, G.; de Meijere, A. Synthesis 1989, 359363.
36. Melgar-Fernández, R.; González-Olvera, R.; Juaristi, E. Tetrahedron 2005, 61, 4329-4333.
37. Rovnyak, G. C. US Patent 4,220,791. 1980.
38. López, R., H. PhD Thesis. CINVESTAV-IPN. México: 2000.
39. Aviña, V., J. A. PhD Thesis. CINVESTAV-IPN. México: 2004.
2. Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett. 1986, 27, 279-282.
3. Giguere, R. J.; Bray, T. L.; Duncan, S. M.; Majetich, G. Tetrahedron Lett. 1986, 27, 4945-4948.
4. Kappe, C. O.; Dallinger, D. Nature Reviews Drug Discovery 2006, 5, 51-63.
5. a) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105; b) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717-727; c) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250-6284; d) de la Hoz, A.; Díaz-Ortiz, A.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164-178; e) Collins, J. M.; Leadbeater, N. E. Org. Biomol. Chem. 2007, 5, 1141-1150; f) Dallinger, D.; Kappe, O. Chem. Rev. 2007, 107, 2563-2591; g) Appukkuttan, P.; Van der Eycken, E. Eur. J. Org. Chem. 2008, 1133-1155; h) Polshettiwar, V.; Varma, R. S. Acc. Chem. Res. 2008, 41, 629-639; i) Polshettiwar, V.; Varma, R. S. Chem. Soc. Rev. 2008, 37, 1546-1557.
6. Jainta, M.; Niegre, M.; Bräse, S. Eur. J. Org. Chem. 2008, 54185424.
7. Donets, P. A.; Goeman, J. L.; Van der Eycken, J.; Robeyns, K.; Van Meervelt, L.; Van der Eycken, E. V. Eur. J. Org. Chem. 2009, 793-796.
8. Espinoza-Moraga, M.; Caceres, A. G.; Santos, L. S. Tetrahedron Lett. 2009, 50, 7059-7061.
9. Genov, M.; Almorín, A.; Espinet, P. Tetrahedron: Asymmetry 2007, 18, 625-627.
10. a) Westermann, B.; Neuhaus, C. Angew. Chem. Int. Ed. 2005, 44, 4077-4079; b) Rodríguez, B.; Bolm, C. J. Org. Chem. 2006, 71, 2888-2891; c) Hosseini, M.; Stiasni, N.; Barbieri, V.; Kappe, C. O. J. Org. Chem. 2007, 72, 1417-1424.
11. Mossé, S.; Alexakis, A. Org. Lett. 2006, 8, 3577-3580.
12. Baumann, T.; Bächle, M.; Hartmann, C.; Bräse, S. Eur. J. Org. Chem. 2008, 2207-2212.
13. Genov, M.; Salas, G.; Espinet, P. J. Organomet. Chem. 2008, 693, 2017-2020.
14. Melgar-Fernández, R.; González-Olvera, R.; Olivares-Romero, J. L.; González-López, V.; Romero-Ponce, L.; Ramírez-Zárate, M. R.; Demare, P.; Regla, I.; Juaristi, E. Eur. J. Org. Chem. 2008, 655-672.
15. a) Portoghese, P. S.; Mikhail, A. A. J. Org. Chem. 1966, 31, 10591062; b) Braish, T. F.; Fox, D. E. J. Org. Chem. 1990, 55, 16841687.
16. a) Hoppe, D.; Hense, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316; b) Schütz, T. Synlett 2003, 901-902.
17. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360-416.
18. González-Olvera, R.; Demare, P.; Regla, I.; Juaristi, E. ARKIVOC 2008, 6, 61-72.
19. Stadler, A.; Kappe, C. O. J. Chem. Soc. Perkin Trans. 2 2000, 1363-1368.
20. a) Asami, M.; Sato, S.; Watanabe, H. Chem. Lett. 2000, 990-991; b) Sato, S.; Watanabe, H.; Asami, M. Tetrahedron: Asymmetry 2000, 11, 4329-4340; c) Basavaiah, D.; Rao, K. V.; Reddy, B. S. Tetrahedron: Asymmetry 2006, 17, 1041-1044; d) Basavaiah, D.; Rao, K. V.; Reddy, B. S. Tetrahedron: Asymmetry 2007, 18, 968974.
21. Olivares-Romero, J. L.; Juaristi, E. Tetrahedron 2008, 64, 99929998.
22. See for example: Kappe, C. O. Microwaves in Organic and Medicinal Chemistry. Wiley-VCH, Weinheim: 2005.
23. a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553; b) Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861-2863.
24. See for example: Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138-5175.
25. Ficken, G. E. US Patent 3,153,654. 1964.
26. Luppi, G.; Cozzi, P. G.; Monari, M.; Kaptein, B.; Broxterman, Q. B.; Tomasini, C. J. Org. Chem. 2005, 70, 7418-7421.
27. Kimura, S. Org. Biomol. Chem. 2008, 6, 1143-1148.
28. Juaristi, E.; Aviña, J. Pure Appl. Chem. 2005, 77, 1235-1241.
29. a) Klein, S.; Czekaj, M.; Molino, B.; Chu, V. Bioorg. Med. Chem. Lett. 1997, 7, 1773-1778; b) Cardillo, G.; Gentilucci, L.; Melchiorre, P.; Spampinato, S. Bioorg. Med. Chem. Lett. 2000, 10, 2755-2758; c) Sagan, S.; Milcent, T.; Ponsinet, R.; Convert, O.; Tasseau, O.; Chassaing, G.; Lavielle, S.; Lequin, O. Eur. J. Biochem. 2003, 270, 939-949; d) Szeto, H. H.; Schiller, P. W.; Zhao, K.; Luo, G. FASEB Journal 2004, 19, 118-120; e) Lind, R.; Greenhow, D.; Perry, S.; Kimmerlin, T.; Seebach, D. Chem. & Biodiversity 2004, 1, 1391-1400; f) Seebach, D.; Rueping, M.; Ardvidsson, P. I.; Kimmerlin, T.; Micuch, P.; Noti, C.; Langenegger, D.; Hoyer, D. Helv. Chim. Acta 2001, 84, 35033510; g) Epand, R. F.; Schmitt, M. A.; Gellman, S. H.; Sen, A.; Auger, M.; Hughes, D. W.; Epand, R. M. Mol. Membrane Biol. 2005, 22, 457-469; h) Mollica, A.; Paradisi, M. P.; Torino, D.; Spisani, S.; Lucente, G. Amino Acids 2006, 30, 453-459.
30. See for example: a) Reyes-Rangel, G.; Jiménez-González, E.; Olivares-Romero, J. L.; Juaristi, E. Tetrahedron: Asymmetry 2008, 19, 2839-2849; b) Ávila-Ortiz, C. G.; Reyes-Rangel, G.; Juaristi, E. Tetrahedron 2005, 61, 8372-8381; c) Castellanos, E.; Reyes-Rangel, G.; Juaristi, E. Helv. Chim. Acta 2004, 87, 10161024; d) Gutiérrez-García, V. M.; Reyes-Rangel, G.; MuñozMuñiz, O.; Juaristi, E. Helv. Chim. Acta 2002, 85, 4189-4199; e) Gutiérrez-García, V. M.; López-Ruiz, H.; Reyes-Rangel, G.; Juaristi, E. Tetrahedron 2001, 57, 6487-6496; f) Juaristi, E.; Balderas, M.; López-Ruiz, H.; Jiménez-Pérez, V. M.; KaiserCarril, M. L.; Ramírez-Quiros, Y. Tetrahedron: Asymmetry 1999, 10, 3493-3505.
31. Escalante, J.; González-Tototzin, M. A.; Aviña, J.; Muñoz-Muñiz, O.; Juaristi, E. Tetrahedron 2001, 57, 1883-1890.
32. Crystal data for 19: C22H26N2O2, monoclinic, space group P 2(1), a = 10.9924(11)Å, b = 6.5469(19)Å, c = 13.2954(09)Å, α = γ = 90°, β = 96.4848(68)°, V = 950.6Å3, crystal size: 0.3 × 0.2 × 0.1 mm3, R1 = 0.0441 (wR2 = 0.1087). Crystal data for 21: C22H26N2S2, monoclinic, space group P 2(1), a = 12.56660(50)Å, b = 6.03300(20)Å, c = 13.00150(59)Å, α = γ = 90°, β = 92.3405(15)°, V = 984.8776(68)Å3, crystal size: 0.88x0.20x0.15 mm3, R1 = 0.0427 (wR2 = 0.1223). Crystal data for 29: C23H23NO2, monoclinic, space group P 2(1), a = 9.8525(20)Å, b = 6.0365(12)Å, c = 16.2635(33)Å, α = γ = 90°, β = 104.788(30)°, V = 935.225Å3, crystal size: 0.3 × 0.2 × 0.1 mm3, R1 = 0.0379 (wR2 = 0.0932). CCDC 740273 (19), CCDC 740274 (21), and CCDC 740275 (29) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via http://www.ccdc.cam.ac.uk/data_request/cif.
33. Guzmán-Mejía, R.; Reyes-Rangel, G.; Juaristi, E. Nature Protocols 2007, 2, 2759-2766.
34. Díaz-Sánchez, B.; Iglesias-Arteaga, M.; Melgar-Fernández, R.; Juaristi, E. J. Org. Chem. 2007, 72, 4822-4825.
35. Wessjohann, L.; Mcgaffin, G.; de Meijere, A. Synthesis 1989, 359363.
36. Melgar-Fernández, R.; González-Olvera, R.; Juaristi, E. Tetrahedron 2005, 61, 4329-4333.
37. Rovnyak, G. C. US Patent 4,220,791. 1980.
38. López, R., H. PhD Thesis. CINVESTAV-IPN. México: 2000.
39. Aviña, V., J. A. PhD Thesis. CINVESTAV-IPN. México: 2004.
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