Computational study on the cyclopropanation reaction of ylides generated from α-pyridiniumacetates

Heterocycles

Volumn 81, Issue 11, 2010, Pages 2479-2495

  Matsumura, Shuji ^a,b   Takagi, Ryukichi ^b   Kojima, Satoshi ^b   Ohkata, Katsuo ^b   Abe, Manabu ^b  

^a OTSUKA PHARMACEUTICAL CO LTD   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79951469956     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-10-11926     Document Type: Article

References (75)

1. For general reviews on cyclopropanes: a) Z. Rappoport, ed., The Chemistry of the Cyclopropyl Group, Wiley: New York, 1987.
2. J. Salaün, Chem. Rev., 1989, 89, 1247.
3. A. de Meijere, ed., Carbocyclic Three-and Four Membered Ring Compounds, Houben-Weyl Vol. E17a-c, Thieme: Stuttgart, 1996.
4. For reactions of cyclopropanes see: a) S. Danishefsky, Acc. Chem. Res., 1979, 12, 66 and references therein.
5. A. de Meijere, Angew. Chem., Int. Ed. Engl., 1979, 18, 809.
6. H. N. C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, J. Tanko, and T. Hudlicky, Chem. Rev., 1989, 89, 165.
7. For reviews: a) J. Salaün, In Small Ring Compounds in Organic Synthesis V, Topics in Current Chemistry, Vol. 207, Spinger-Verlag: Berlin, 2000, pp. 1-67.
8. J. Pietruszka, Chem. Rev., 2003, 103, 1051.
9. For reviews: a) A.-H. Li, L.-X. Dai, and V. K. Aggarwal, Chem. Rev., 1997, 97, 2341.
10. H. Lebel, J.-F. Marcoux, C. Molinaro, and A. B. Charette, Chem. Rev., 2003, 103, 977.
11. V. K. Aggarwal and C. L. Winn, Acc. Chem. Res., 2004, 37, 611.
12. a) S. Arai, K. Nakayama, T. Ishida, and T. Shioiri, Tetrahedron Lett., 1999, 40, 4215.
13. N. Vignola and B. List, J. Am. Chem. Soc., 2004, 126, 450.
14. S. H. McCooey, T. McCabe, and S. J. Connon, J. Org. Chem., 2006, 71, 7494.
15. R. Rios, H. Sunden, J. Vesely, G.-L. Zhao, P. Dziedzic, and A. Cordova, Adv. Synth. Catal., 2007, 349, 1028.
16. H. Xie, L. Zu, H. Li, J. Wang, and W. Wang, J. Am. Chem. Soc., 2007, 129, 10886.
17. S. Kojima, M. Suzuki, A. Watanabe, and K. Ohkata, Tetrahedron Lett., 2006, 47, 9061.
18. a) V. K. Aggarwal, E. Alonso, G. Fang, M. Ferrara, G. Hynd, and M. Porcelloni, Angew. Chem. Int. Ed., 2001, 40, 1430.
19. R. K. Kunz and D. W. C. MacMillan, J. Am. Chem. Soc., 2005, 127, 3240.
20. A. Hartikka and P. I. Arvidsson, J. Org. Chem., 2007, 72, 5874.
21. A. Hartikka, A. T. Ślósarczyk, and P. I. Arvidsson, Tetrahedron: Asymmetry, 2007, 18, 1403.
22. Y.-H. Zhao, G. Zhao, and W.-G. Cao, Tetrahedron: Asymmetry, 2007, 18, 2462.
23. a) C. D. Papageorgiou, S. V. Ley, and M. J. Gaunt, Angew. Chem. Int. Ed., 2003, 42, 828.
24. N. Bremeyer, S. C. Smith, S. V. Ley, and M. J. Gaunt, Angew. Chem. Int. Ed., 2004, 43, 2681.
25. C. D. Papageorgiou, M. A. C. de Dios, S. V. Ley, and M. J. Gaunt, Angew. Chem. Int. Ed., 2004, 43, 4641.
26. C. C. C. Johansson, N. Bremeyer, S. V. Ley, D. R. Owen, S. C. Smith, and M. J. Gaunt, Angew. Chem. Int. Ed., 2006, 45, 6024.
27. For some recent reviews involving azomethine ylide cycloaddition see: a) A. Padwa and W. H. Pearson, eds. Synthetic Applications of 1, 3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, The Chemistry of Heterocyclic Compounds Vol. 59, Wiley: New York, 2003.
28. T. M. V. D. Pinho e Melo, Eur. J. Org. Chem., 2006, 2873.
29. C. N. Ljera and J. M. Sansano, Curr. Org. Chem., 2003, 7, 1105.
30. S. Kanemasa, Synlett, 2002, 1371.
31. K. V. Gothelf, In Cycloaddition Reactions in Organic Synthesis, S. Kobayashi, and K. A. Jorgensen, eds.; Wiley-VCH: Weinheim, 2002, pp. 211-245.
32. C. Najera and J. M. Sansano, Angew. Chem. Int. Ed., 2005, 44, 6272.
33. I. Coldham and R. Hufton, Chem. Rev., 2005, 105, 2765.
34. S. Husinec and V. Savic, Tetrahedron: Asymmetry, 2005, 16, 2047.
35. K. V. Gothelf and K. A. Jorgensen, Chem. Rev., 1998, 98, 863.
36. G. Pandey, P. Banerjee, and S. R. Gadre, Chem. Rev., 2006, 106, 4484.
37. a) A. M. Shestopalov, Y. A. Sharanin, V. P. Litvinov, and O. M. Nefedov, Zh. Org. Khim., 1989, 25, 1111.
38. V. P. Litvinov, A. M. Shestopalov, Y. A. Sharanin, and V. Y. Mortikov, Dokl. Akad. Nauk SSSR, 1989, 309, 115.
39. A. M. Shestopalov, V. P. Litvinov, L. A. Rodinovskaya, and Y. A. Sharanin, Izv. Acad. Nauk SSSR, Ser. Khim., 1991, 1, 146.
40. V. P. Litvinov and A. M. Shestopalov, Zh. Org. Khim., 1997, 33, 975 and references cited therein.
41. N. H. Vo, C. J. Eyermann, and C. N. Hodge, Tetrahedron Lett., 1997, 38, 7951.
42. A. M. Shestopalov, A. A. Shestopalov, and L. A. Rodinovskaya, Synthesis, 2008, 1.
43. a) S. Kojima, K. Fujitomo, Y. Shinohara, M. Shimizu, and K. Ohkata, Tetrahedron Lett., 2000, 41, 9847.
44. S. Kojima, K. Hiroike, and K. Ohkata, Tetrahedron Lett., 2004, 45, 3565.
45. S. Kojima, K. Fujitomo, Y. Itoh, K. Hiroike, M. Murakami, and K. Ohkata, Heterocycles, 2006, 67, 679.
46. S. Yamada, J. Yamamoto, and E. Ohta, Tetrahedron Lett., 2007, 48, 855.
47. Spartan'04 and Spartan'06, Wavefunction Inc., Irvine, CA. Spartan, version 2.0; Wavefunction: Irvine, CA, 2001.
48. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Zakrzewski, V. J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
49. a) O. Tsuge, S. Kanemasa, and S. Takenaka, Bull. Chem. Soc. Jpn., 1986, 59, 3631.
50. O. Tsuge, S. Kanemasa, and S. Takenaka, Bull. Chem. Soc. Jpn., 1987, 60, 1489.
51. O. Tsuge, S. Kanemasa, K. Sakamoto, and S. Takenaka, Bull. Chem. Soc. Jpn., 1988, 61, 2513.
52. a) Gh. Surpateanu, M. Constantinescu, C. Luchian, M. Petrovani, I. Zugravescu, and A. Lablache-Combier, Rev. Roum. Chim., 1981, 26, 1169.
53. M. Constantinescu, G. Surpateanu, C. Luchian, M. Petrovanu, and I. Zugravescu, Rev. Roum. Chim., 1981, 26, 1451.
54. G. Surpateanu, M. Constantinescu, C. Luchian, M. Petrovanu, I. Zugravescu, and A. Lablache-Combier, Rev. Roum. Chim., 1983, 28, 831.
55. G. Surpateanu, M. Constantinescu, C. Luchian, M. Petrovanu, I. Zugravescu, and A. Lablache-Combier, Rev. Roum. Chim., 1983, 28, 933.
56. J. M. Minguez, M. I. Castellote, J. J. Vaquero, J. L. Garcia-Navio, J. Alvarez-Builla, O. Castano, and J. L. Andres, J. Org. Chem., 1996, 61, 4655.
57. Y. Karzaz, G. Vergoten, and G. Surpateanu, J. Mol. Struct., 1998, 471, 83.
58. Y. Karzazi, G. Vergoten, and G. Surpateanu, J. Mol. Struct., 1999, 476, 105.
59. K. Elender, P. Riebel, A. Weber, and J. Sauer, Tetrahedron, 2000, 56, 4261.
60. K. Matsumoto, N. Hayashi, Y. Ikemi, M. Toda, T. Uchida, K. Aoyama, and Y. Miyakoshi, J. Heterocycl. Chem., 2001, 38, 371.
61. R. N. Butler, A. G. Coyne, P. McArdle, D. Cunningham, and L. A. Burke, J. Chem. Soc., Perkin Trans. 1, 2001, 1391.
62. P. C. Iuhas, F. Georgescu, E. Georgescu, C. Draghici, and M. T. Caproiu, Rev. Roum. Chim., 2003, 47, 333.
63. Y. Liu, H.-Y. Hu, Q.-J. Liu, H.-W. Hu, and J.-H. Xu, Tetrahedron, 2007, 63, 2024.
64. J. Valenciano, A. M. Cuadro, J. J. Vaquero, J. Alvarez-Builla, R. Palmeiro, and O. Castaño, J. Org. Chem., 1999, 64, 9001.
65. R. N. Butler, A. G. Coyne, and L. A. Burke, J. Chem. Soc., Perkin Trans. 2, 2001, 1781.
66. T. Matsuoka and K. Harano, Tetrahedron, 1995, 51, 6451.
67. For a recent review on theoretical treatment of dipolar cycloaddition see: D. H. Ess, G. O. Jones, and K. N. Houk, Adv. Synth. Catal., 2006, 348, 2337.
68. For recent examples on the cycloaddition reaction of azomethine ylides see: M. J. Aurell, L. R. Domingo, P. Pérez, and R. Contreras, Tetrahedron, 2004, 60, 11503 and references therein.
69. Metalated N: a) F. Neumann, C. Lambert, and P. von R. Schleyer, J. Am. Chem. Soc., 1998, 120, 3357.
70. A. Zubia, L. Mendoza, S. Vivanco, E. Aldaba, T. Carrascal, B. Lecea, A. Arrieta, T. Zimmerman, F. Vidal-Vanaclocha, and F. P. Cossío, Angew. Chem. Int. Ed., 2005, 44, 2903.
71. X.-X. Yan, Q. Peng, Y. Zhang, K. Zhang, W. Hong, X.-L. Hou, and Y.-D. Wu, Angew. Chem. Int. Ed., 2006, 45, 1979.
72. S. Vivanco, B. Lecea, A. Arrieta, P. Prieto, I. Morao, A. Linden, and F. P. Cossío, J. Am. Chem. Soc., 2000, 122, 6078.
73. a) K. Kavitha and P. Venuvanalingam, J. Chem. Soc., Perkin Trans 2, 2002, 2130.
74. K. Kavitha, M. Manoharan, and P. Venuvanalingam, J. Org. Chem., 2005, 70, 2528.
75. K. Kavitha and P. Venuvanalingam, Int. J. Quantum Chem., 2005, 104, 64.