N -(2-Pyridylmethyl)imines as azomethine precursors in catalytic asymmetric [3 + 2] cycloadditions

Organic Letters

Volumn 12, Issue 24, 2010, Pages 5608-5611

  Padilla, Silvia ^a   Tejero, Rubén ^a   Adrio, Javier ^a   Carretero, Juan C ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78650413360     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102605q     Document Type: Article

References (51)

1. For pioneering references, see
2. Longmire, J. M.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 13400-13401
3. Gothelf, A. S.; Gothelf, K. V.; Hazell, R. J.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 4236-4238
4. For recent reviews, see
5. Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887
6. Pellisier, H. Tetrahedron 2007, 63, 3235-3285
7. Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484-4517
8. Nájera, C.; Sansano, J. M. Angew. Chem., Int. Ed. 2005, 44, 6272-6276
9. For selected recent references, Cu-catalysts, see
10. Robles-Machín, R.; González-Esguevillas, M.; Adrio, J.; Carretero, J. C. J. Org. Chem. 2010, 75, 233-236
11. Arai, T.; Mishiro, A.; Yokoyama, N.; Suzuki, K.; Sato, H. J. Am. Chem. Soc. 2010, 132, 5338-5339
12. Kim, H. Y.; Shih, H.-Y.; Knabe, W. E.; Oh, K. Angew. Chem., Int. Ed. 2009, 48, 7420-7423
13. Filippone, S.; Maroto, E. E.; Martín-Domenech, A.; Suarez, M.; Martín, N. Nature Chem. 2009, 1, 578-582
14. Hernandez-Toribio, J.; Gómez Arrayás, R.; Martín-Matute, B.; Carretero, J. C. Org. Lett. 2009, 11, 393-396
15. López-Pérez, A.; Adrio, J.; Carretero, J. C. Angew. Chem., Int. Ed. 2009, 48, 340-343
16. López-Pérez, A.; Adrio, J.; Carretero, J. C. J. Am. Chem. Soc. 2008, 130, 10084-10085
17. Wang, C.-J.; Liang, G.; Xue, Z.-Y.; Gao, F. J. Am. Chem. Soc. 2008, 130, 17250-17251
18. Fukuzawa, S.-I.; Oki, H. Org. Lett. 2008, 10, 1747-1750
19. Yan, X.-X.; Peng, Q.; Zhang, Y.; Zhang, K.; Hong, W.; Hou, X.-L.; Wu, Y.-D. Angew. Chem., Int. Ed. 2006, 45, 1979-1983 Ag-catalysts: Shimizu, K.; Ogata, K.; Fukuzawa, S.-i. Tetrahedron Lett. 2010, 51, 5068-5070
20. Oura, I.; Shimizu, K.; Ogata, K.; Fukuzawa, S.-i. Org. Lett. 2010, 12, 1752-1755
21. Xue, Z.-Y.; Liu, T.-L.; Lu, Z.; Huang, H.; Tao, H.-Y.; Wang, C.-J. Chem. Commun. 2010, 46, 1727-1729
22. Yu, S.-B.; Hu, X.-P.; Deng, J.; Wang, D.-Y.; Duan, Z.-C.; Zheng, Z. Tetrahedron: Asymmetry 2009, 20, 621-625
23. Wang, C.-J.; Xue, Z.-Y.; Liang, G.; Zhou, L. Chem. Commun. 2009, 2905-2907
24. Nájera, C.; de Gracia Retamosa, M.; Sansano, J. M.; de Cozar, J. M.; Cossío, F. P. Tetrahedron: Asymmetry 2008, 19, 2913-2933
25. Nájera, C.; de Gracia Retamosa, M.; Sansano, J. M. Angew. Chem., Int. Ed. 2008, 47, 6055-6058 Zn-catalysts Dogan, O.; Koyuncu, H.; Garner, P.; Bulut, A.; Youngs, W. J.; Panzner, M. Org. Lett. 2006, 8, 4687-4690 Ni-catalysts Arai, T.; Yokoyama, N.; Mishiro, A.; Sato, H. Angew. Chem., Int. Ed. 2010, 49, 7895-7898
26. Shi, J.-W.; Zhao, M.-X.; Lei, Z.-Y.; Shi, M. J. Org. Chem. 2008, 73, 305-308 Ca-catalysts Tsubogo, T.; Saito, S.; Seki, K.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2008, 130, 13321-13332
27. For selected organocatalytic asymmetric versions of this reaction, see
28. Liu, Y.-K.; Liu, H.; Du, W.; Yue, L.; Chen, Y.-C. Chem. - Eur. J. 2008, 14, 9873-9877
29. Xue, M.-X.; Zhang, X.-M.; Gong, L.-Z. Synlett 2008, 691-694
30. Chen, X.-H.; Zhang, W.-Q.; Gong, L.-Z. J. Am. Chem. Soc. 2008, 130, 5652-5654
31. Ibrahem, I.; Ríos, R.; Vesely, J.; Córdova, A. Tetrahedron Lett. 2007, 48, 6252-6257
32. Vicario, J. L.; Reboredo, S.; Badía, D.; Carrillo, L. Angew. Chem., Int. Ed. 2007, 46, 5168-5170
33. Alemparte, C.; Blay, G.; Jørgensen, K. A. Org. Lett. 2005, 7, 4569-4572
34. Yamashita, Y.; Guo, X.-X.; Takashita, R.; Kobayashi, S. J. Am. Chem. Soc. 2010, 132, 3262-3263
35. Robles-Machín, R.; Alonso, I.; Adrio, J.; Carretero, J. C. Chem. - Eur. J. 2010, 16, 5286-5291
36. For the non asymmetric thermal 1,3-dipolar cycloaddition of N -(2-pyridylmethyl)imines, see
37. Grigg, R.; Donegan, G.; Gunaratne, H. Q. N.; Kennedy, D. A.; Malone, J. F.; Sridharan, V.; Thianatanagul, S. Tetrahedron 1989, 45, 1723-1746
38. Stohler, R.; Wahl, F.; Pfaltz, A. Synthesis 2005, 1431-1436
39. See for example
40. Xu, D.-Z.; Shi, S.; Wang, Y. Eur. J. Org. Chem. 2009, 4848-4853
41. Comba, P.; Lang, C.; Lopez de Laorden, C.; Muruganantham, A.; Rajaraman, G.; Wadepohl, H.; Zajaczkowski, M. Chem. - Eur. J. 2008, 14, 5313-5328
42. Ishii, T.; Fujioka, S.; Sekiguchi, Y.; Kotsui, H. J. Am. Chem. Soc. 2004, 126, 9558-9559
43. Dickerson, T. J.; Janda, K. D. J. Am. Chem. Soc. 2002, 124, 320-321
44. See Supporting Information for catalyst optimization studies.
45. For a recent example on the use of the 2-pyridine unit as activating group in asymmetric metal catalyzed reactions, see
46. Rupnicki, L.; Saxena, A.; Lam, H. W. J. Am. Chem. Soc. 2009, 131, 10386-10387
47. . The resulting residue was purified by silica gel flash chromatography (hexane-EtOAc 1:2) to afford exo-2a (70.5 mg, 85%, white solid).
48. See Supporting Information for details of the X-ray structure of exo-2g, exo -10g, and exo-11g. CCDC 784831, CCDC 784832, and CCDC 784833 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data-request/cif.
49. By analogy with the 1,3-dipolar cycloaddition of -iminoesters, exo refers to the pyrrolidine adduct with trans stereochemistry at C2 - C3.
50. For catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with nitroalkenes, see: refs 3b and 3j.
51. For the use of enones as dipolarophiles, see refs 3e and 3l.