A combined experimental and theoretical study of the polar [3 + 2] cyeloaddition of electrophilically activated carbonyl ylides with aldehydes and imines

Journal of Organic Chemistry

Volumn 74, Issue 5, 2009, Pages 2120-2133

  Bentabed Ababsa, Ghenia ^a,b   Derdour, Aicha ^b   Roisnel, Thierry ^c   Sáez, Jose A ^d   Pérez, Patricia ^e   Chamorro, Eduardo ^e   Domingo, Luis R ^d   Mongin, Florence ^a  

^a Chimie et Photonique Moleculaires Rennes   (France)

^b UNIVERSITÉ DES SCIENCES ET DE LA TECHNOLOGIE D ORAN MOHAMED BOUDIAF   (Algeria)

^c INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^d UNIVERSITY OF VALENCIA   (Spain)

^e UNIVERSIDAD ANDRÉS BELLO   (Chile)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CHARGE TRANSFER; MICROWAVE IRRADIATION;

CARBONYL YLIDE; CYCLOADDITION REACTION; CYCLOADDITIONS; ELECTROPHILIC CHARACTER; NUCLEOPHILIC ATTACK; REACTIVITY INDICES; THEORETICAL STUDY; TRANSITION STRUCTURES;

CYCLOADDITION;

ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; IMINE; NITRILE; NITROGEN; OXYGEN;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; MICROWAVE RADIATION; OUTCOME ASSESSMENT; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; THEORETICAL STUDY;

EID: 64249166380     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8027104     Document Type: Article

References (76)

1. Huisgen, R.; Grashey, R; Sauer, J. In The Chemistry of Alkenes; Interscience: New York, 1964.
2. (a) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vols. 1,2.
3. (b) Gothelf, K. V.; Jorgenson, K. A. Chem. Rev. 1998, 98, 863-909.
4. (c) Harwood, L. M.; Vickers, R. J. In The Chemistry of Heterocyclic Compounds: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.,Pearson, W. H., Eds.; Wiley and Sons: New York, 2002.
5. See for example: (a) Bera, S.; Malik, L.; Bhat, B.; Caroll, S. S.; Hrin, R.; MacCoss, M.; McMasters, D. R.; Miller, M. D.; Moyer, G.; Olsen, D. B.; Schleif, W. A.; Tomassini, J. E.; Eldrup, A. B. Bioorg. Med. Chem. 2004, 12, 6237-6247.
6. (b) Liang, Y.; Narayanasamy, J.; Schinazi, R. F.; Chu, C. K. Bioorg. Med. Chem. 2006, 14, 2178-2189.
7. (c) Wender, P. A.; Verma, V. A. Org. Lett. 2006, 8, 1893-1896.
8. (d) Schmidt, M.; Ungvári, J.; Glóde, J.; Dobner, B.; Langner, A. Bioorg. Med. Chem. 2007, 15, 2283-2297.
9. See for example: (a) Tuchscherer, G.; Grell, D.; Tatsu, Y.; Durieux, P.; Fernandez-Carneado, J.; Hengst, B.; Kardinal, C.; Feller, S. Angew. Chem., Int. Ed. 2001, 40, 2844-2848.
10. (b) Cheng, Q.; Kiyota, H.; Yamaguchi, M.; Horiguchi, T.; Oritani, T. Bioorg. Med. Chem. Lett. 2003, 13, 1075-1077.
11. (c) Botta, M.; Armaroli, S.; Castagnolo, D.; Fontana, G.; Pera, P.; Bombardelli, E. Bioorg. Med. Chem. Lett. 2007, 17, 1579-1583.
12. (d) Pasteris, R. J.; Hanagan, M. A.; Shapiro, R. PCT Int. Appl. WO 2008013622 A2 20080131, 2008.
13. (a) Robert, A.; Pommeret, J. J.; Foucaud, A. Tetrahedron Lett. 1971, 12, 231-234.
14. (b) Robert, A.; Pommeret, J. J.; Foucaud, A. Tetrahedron 1972, 28, 2085-2097. Concerning the Rh2(OAc)4-catalyzed synthesis of 2,5-diaryl-1,3-dioxolane, see for example:
15. (c) Jiang, B.; Zhang, X.; Luo, Z. Org. Lett. 2002, 4, 2453-2455.
16. (d) Russell, A. E.; Brekan, J.; Gronenberg, L.; Doyle, M. P. J. Org. Chem. 2004, 69, 5269-5274.
17. (e) Lu, C.-D.; Chen, Z.-Y.; Liu, H.; Hu, W.-H.; Mi, A.-Q. Org. Lett. 2004, 6, 3071-3074.
18. (a) Pommeret, J. J.; Robert, A. C.R. Acad. Sci. Paris, Ser. C 1971, 272, 333-336.
19. (b) Robert, A.; Pommeret, J. J.; Marchand, E.; Foucaud, A. Tetrahedron 1973, 29, 463-468.
20. Bentabed-Ababsa, G.; Derdour, A.; Roisnel, T.; Sáez, J. A.; Domingo, L. R.; Mongin, F. Org. Biomol. Chem. 2008, 6, 3144-3157.
21. Sliwnska, A.; Czardybon, W.; Warkentin, J. Org. Lett. 2007, 9, 695-698.
22. Preliminary studies have previously been reported: Bentabed, G.; Rahmouni, M.; Mongin, F.; Derdour, A.; Hamelin, J.; Bazureau, J. P. Synth. Commun. 2007, 37, 2935-2948.
23. Baudy, M.; Robert, A.; Foucaud, A. J. Org. Chem. 1978, 43, 3732-3736.
24. (a) de la Hoz, A.; D?́az-Ortiz, A.; Langa, F. In Microwave in Organic Synthesis, 1st ed.; Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 9.
25. (b) Bougrin, K.; Soufiaoui, M.; Bashiardes, G. In Microwave in Organic Synthesis, 2nd ed.; Loupy, A., Ed.;Wiley-VCH: Weinheim, Germany, 2006; Vol. 1, Chapter 11.
26. Using a monomode reactor (Prolabo Synthewave 402) with accurate control of power and temperature (infrared detection).
27. Note that the reactions did not proceed cleanly when the reactants were heated without solvent in an oil bath.
28. Note that H5 is shifted towards high fields when a 1-naphthyl group is present at the 5 position of the dioxolane ring.
29. Chérouvrier, J.-R.; Carreaux. F.; Bazureau, J. P. Tetrahedron Lett. 2002, 43, 3581-3584.
30. (a) Domingo, L. R.; Aurell, M. J.; Perez, P.; Contreras, R. Tetrahedron 2002, 58, 4417-4423.
31. (b) Pérez, P.; Domingo, L. R.; Aizman, A.; Contreras, R. In Theoretical Aspects of Chemical Reactivity; Toro-Labbé, A., Ed.; Elsevier Science: New York, 2007; Vol. 19, pp 139-201.
32. Pérez, P.; Domingo, L. R.; Aurell, M. J.; Contreras, R. Tetrahedron 2003, 59, 3117-3125.
33. (a) Geerlings, P.; De Proft, F.; Langenaeker, W. Chem. Rev. 2003, 103, 1793-1873.
34. (b) Ess, D. H.; Jones, G. O.; Houk, K. N. Adv. Synth. Catal. 2006, 348, 2337-2361.
35. Parr, R. G.; von Szentpaly. L.; Liu, S. J. Am. Chem. Soc. 1999. 121, 1922-1924.
36. Domingo, L. R.; Chamorro, E.; Perez, P. J. Org. Chem. 2008, 73, 4615-4624.
37. (a) Domingo, L. R. Eur. J. Org. Chem. 2004, 4788-4793.
38. (b) Domingo, L. R.; Chamorro, E.; Perez, P. J. Phys. Chem. A 2008, 112, 4046-4053.
39. Domingo, L. R.; Aurell, M. J.; Perez, P.; Contreras, R. J. Phys. Chem. A 2002, 106, 6871-6875.
40. Parr, R. G.; Yang, W. J. Am. Chem. Soc. 1984, 106, 4049-4050.
41. Pérez, P.; Domingo, L. R.; Duque, M.; Chamorro, E. J. Mol. Struct. (THEOCHEM) 2009, 895, 86-91.
42. Wiberg, K. B. Tetrahedron 1968, 24, 1083-1096.
43. Domingo, L. R; Saéz. J. A.; Zaragoza. R. A.; Arno, M. Chem. 2008, 73, 8791-8799.
44. (a) Savin, A.; Becke, A. D.; Flad, J.; Nesper, R.; Preuss, H.; Vonschnering, H. G. Angew. Chem., Int. Ed. Engl. 1991, 30, 409-412.
45. (b) Savin, A.; Silvi, B.; Colonna, F. Can. J. Chem. 1996, 74, 1088-1096.
46. (c) Savin, A.; Nesper, R.; Wengert, S.; Fassler, T. F. Angew. Chem., Int. Ed. Engl. 1997, 36, 1809-1832.
47. (d) Silvi, B. J. Mol. Struct. 2002, 614, 3-10.
48. (a) Bader, R. F. W.; Stephens, M. E. J. Am. Chem. Soc. 1975, 97, 7391-7399.
49. (b) Fradera, X.; Austen, M. A.; Bader, R. F. W. J. Phys. Chem. A 1999, 103, 304-314.
50. (c) Silvi, B. Phys. Chem. Phys. 2004, 6, 256-260.
51. (a) Chamorro, E. J. Chem. Phys. 2003, 118, 8687-8698.
52. (b) Chamorro, E.; Notario, R. J. Phys. Chem. B 2005, 109, 7594-7595.
53. (c) Fuentealba, P.; Chamorro, E.; Santos, J. C. In Theoretical Aspects of Chemical ReactiVity; Toro-Labbe, A., Ed.; Elsevier: Amsterdam, 2006; Vol. 19, p 57.
54. (d) Chamorro, E.; Notario, R.; Santos, J. C.; Pe'rez, P. Chem. Phys. Lett. 2007, 443, 136-140.
55. (a) Berski, S.; Andres, J.; Silvi, B.; Domingo, L. R. J. Phys. Chem. A 2003, 107, 6014-6024.
56. (b) Polo, V.; Domingo, L. R.; Andres, J. J. Phys. Chem. A 2005, 109, 10438-10444.
57. (c) Berski, S.; Andres, J.; Silvi, B.; Domingo, L. R. J. Phys. Chem. A 2006, 110, 13939-13947.
58. (d) Polo, V.; Domingo, L. R.; Andres, J. J. Org. Chem. 2006, 71, 754-762.
59. (e) Domingo, L. R.; Picher, M. T.; Arroyo, P.; Saez, J. A. J. Org. Chem. 2006, 71, 9319-9930.
60. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian03; Gaussian, Inc.: Wallingford CT, 2004.
61. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
62. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
63. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986.
64. Fukui, K. J. Phys. Chem. 1970, 74, 4161-4163.
65. (a) Gonza'lez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
66. (b) González, C.; Schlegel, H. B. J. Chem. Phys. 1991, 95, 5853-5860
67. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
68. (b) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.
69. Noury, S.; Krokidis, X.; Fuster, F.; Silvi, B. Comput. Chem. 1999, 23, 597-604.
70. (a) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094.
71. (b) Simkin, B. Y.; Sheikhet, I. Quantum Chemical and Statistical Theory of Solutions-A Computational Approach; Ellis Harwood: London, 1995.
72. (a) Cances, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032-3041.
73. (b) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327-335.
74. (c) Barone, V.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404-417.
75. (a) Parr, R. G.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512-7516.
76. (b) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.