Unusual ester-directed regiochemical control in endo-selective asymmetric 1,3-dipolar cycloadditions of azomethine ylides with β-sulfonyl acrylates

Chemistry - A European Journal

Volumn 17, Issue 46, 2011, Pages 12922-12927

  Tong, Min Chao ^a   Li, Jun ^a   Tao, Hai Yan ^a   Li, Yu Xue ^b   Wang, Chun Jiang ^a,b  

^a WUHAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

asymmetric catalysis; cycloaddition; density functional calculations; diactivated alkenes; regioselectivity

Indexed keywords

1 ,3-DIPOLAR CYCLOADDITIONS; 1 ,3-DIPOLARCYCLOADDITION; ASYMMETRIC CATALYSIS; AZOMETHINE YLIDES; DENSITY-FUNCTIONAL CALCULATIONS; DIACTIVATED ALKENES; ESTER GROUPS; REGIOCHEMICAL CONTROL; SULFONYL GROUPS; THEORETICAL CALCULATIONS;

CYCLOADDITION; DENSITY FUNCTIONAL THEORY; ESTERS; OLEFINS; REGIOSELECTIVITY; SALTS;

ESTERIFICATION;

ACRYLIC ACID DERIVATIVE; ALKENE; AZO COMPOUND; AZOMETHINE; IMINE; PYRROLE DERIVATIVE; SULFONE; THIOSEMICARBAZONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; THEORETICAL MODEL;

ACRYLATES; ALKENES; AZO COMPOUNDS; CATALYSIS; CYCLIZATION; IMINES; MODELS, THEORETICAL; MOLECULAR STRUCTURE; PYRROLES; STEREOISOMERISM; SULFONES; THIOSEMICARBAZONES;

EID: 80555127296     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102430     Document Type: Article

References (63)

1. L. M. Harwood, R. J. Vickers, in Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products (Eds.:, A. Padwa, W. Pearson,), John Wiley & Sons, New York, 2002.
2. For recent reviews on 1,3-dipolar cycloaddition reactions of azomethine ylides, see: J. Adrio, J. C. Carretero, Chem. Commun. 2011, 47, 6874
3. B. Engels, M. Christl, Angew. Chem. 2009, 121, 8110
4. Angew. Chem. Int. Ed. 2009, 48, 7968
5. L. M. Stanley, M. P. Sibi, Chem. Rev. 2008, 108, 2887
6. M. Úlvarez-Corral, M. Muñoz-Dorado, I. Rodríguez- Garcia, Chem. Rev. 2008, 108, 3174
7. G. Pandey, P. Banerjee, S. R. Gadre, Chem. Rev. 2006, 106, 4484
8. G. Pandey, P. Banerjee, S. R. Gadre, Chem. Rev. 2006, 106, 4484
9. I. Coldham, R. Hufton, Chem. Rev. 2005, 105, 2765.
10. For recent examples on Ag catalysts, see: Y. Yamashita, X.-X. Guo, R. Takashita, S. Kobayashi, J. Am. Chem. Soc. 2010, 132, 3262
11. Y. Yamashita, I. Takaki, S. Kobayashi, Angew. Chem. 2011, 123, 4995
12. Angew. Chem. Int. Ed. 2011, 50, 4893
13. R. Robles-Machín, I. Alonso, J. Adrio, J. C. Carretero, Chem. Eur. J. 2010, 16, 5286
14. I. Oura,;, K. Shimizu, K. Ogata, S.-i. Fukuzawa, Org. Lett. 2010, 12, 1752
15. K. Shimizu, K. Ogata, S.-i. Fukuzawa, Org. Lett. 2010, 12, 1752
16. H. Y. Kim, H.-J. Shih, W. E. Knabe, K. Oh, Angew. Chem. 2009, 121, 7556
17. Angew. Chem. Int. Ed. 2009, 48, 7420
18. C. Nájera, M. de Garcia Retamosa, J. M. Sansano, Angew. Chem. 2008, 120, 6144
19. Angew. Chem. Int. Ed. 2008, 47, 6055
20. W. Zeng, G.-Y. Chen, Y.-G. Zhou, Y.-X. Li, J. Am. Chem. Soc. 2007, 129, 750
21. T. F. Knöpfel, P. Aschwanden, T. Ichikawa, T. Watanabe, E. M. Carreira, Angew. Chem. 2004, 116, 6097
22. Angew. Chem. Int. Ed. 2004, 43, 5971
23. C. Chen, X. Li, S. L. Schreiber, J. Am. Chem. Soc. 2003, 125, 10174
24. J. M. Longmire, B. Wang, X. Zhang, J. Am. Chem. Soc. 2002, 124, 13400.
25. For recent examples on Zn catalysts, see: A. S. Gothelf, K. V. Gothelf, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 2002, 114, 4410
26. Angew. Chem. Int. Ed. 2002, 41, 4236
27. O. Dogan, H. Koyuncu, P. Garner, A. Bulut, W. J. Youngs, M. Panzner, Org. Lett. 2006, 8, 4687.
28. For recent examples on Cu catalysts, see: T. Arai, A. Mishiro, N. Yokoyama, K. Suzuli, H. Sato, J. Am. Chem. Soc. 2010, 132, 5338
29. A. Lõpez-Pérez, J. Adrio, J. C. Carretero, J. Am. Chem. Soc. 2008, 130, 10084
30. S.-i. Fukuzawa, H. Oki, Org. Lett. 2008, 10, 1747
31. S. Cabrera, R. G. Arrayás, B. Martín-Matute, F. P. Cossío, J. C. Carretero, Tetrahedron 2007, 63, 6587
32. M. Shi, J.-W. Shi, Tetrahedron: Asymmetry 2007, 18, 645
33. X.-X. Yan, Q. Peng, Y. Zhang, K. Zhang, W. Hong, X.-L. Hou, Y.-D. Wu, Angew. Chem. 2006, 118, 2013
34. Angew. Chem. Int. Ed. 2006, 45, 1979
35. T. Llamas, R. G. Arrayás, J. C. Carretero, Org. Lett. 2006, 8, 1795
36. S. Cabrera, R. G. Arrayás, J. C. Carretero, J. Am. Chem. Soc. 2005, 127, 16394
37. W. Gao, X. Zhang, M. Raghunath, Org. Lett. 2005, 7, 4241
38. C. Zhang, S.-B. Yu, X.-P. Hu, D.-Y. Wang, Z. Zheng, Org. Lett. 2010, 12, 5542
39. A. P. Antonchick, C. Gerding-Reimers, M. Catarinella, M. Schürmann, H. Preut, S. Ziegler, D. Rauh, H. Waldmann, Nat. Chem. 2010, 2, 735.
40. For recent examples on Ni catalysts, see: T. Arai, N. Yokoyama, A. Mishiro, H. Sato, Angew. Chem. 2010, 122, 8067
41. Angew. Chem. Int. Ed. 2010, 49, 7895
42. J.-W. Shi, M.-X. Zhao, Z.-Y. Lei, M. Shi, J. Org. Chem. 2008, 73, 305.
43. For recent examples on Ca catalysts, see: S. Saito, T. Tsubogo, S. Kobayashi, J. Am. Chem. Soc. 2007, 129, 5364
44. T. Tsubogo, S. Saito, K. Seki, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 2008, 130, 13321.
45. For examples on organocatalysts, see: J. L. Vicario, S. Reboredo, D. Badía, L. Carrillo, Angew. Chem. 2007, 119, 5260
46. Angew. Chem. Int. Ed. 2007, 46, 5168
47. I. Ibrahem, R. Rios, J. Vesely, A. Co'rdova, Tetrahedron Lett. 2007, 48, 6252
48. X.-H. Chen, W.-Q. Zhang, L.-Z. Gong, J. Am. Chem. Soc. 2008, 130, 5652
49. C. Guo, M.-X. Xue, M.-K. Zhu, L.-Z. Gong, Angew. Chem. 2008, 120, 3462
50. Angew. Chem. Int. Ed. 2008, 47, 3414
51. Y-K. Liu, H. Liu, W. Du, L. Yue, Y.-C. Chen, Chem. Eur. J. 2008, 14, 9873.
52. A. Lõpez-Pérez, J. Adrio, J. C. Carretero, Angew. Chem. 2009, 121, 346
53. Angew. Chem. Int. Ed. 2009, 48, 340
54. R. Robles-Machín, M. González-Esguevillas, J. Adrio, J. C. Carretero, J. Org. Chem. 2010, 75, 233.
55. C.-J. Wang, G. Liang, Z.-Y. Xue, F. Gao, J. Am. Chem. Soc. 2008, 130, 17250
56. C.-J. Wang, Z.-Y. Xue, G. Liang, Z. Lu, Chem. Commun. 2009, 2905
57. G. Liang, M.-C. Tong, C.-J. Wang, Adv. Synth. Catal. 2009, 351, 3101
58. Z.-Y. Xue, T.-L. Liu, Z. Lu, H. Huang, H.-Y. Tao, C.-J. Wang, Chem. Commun. 2010, 46, 1727
59. G. Liang, M.-C. Tong, H.-Y. Tao, C.-J. Wang, Adv. Synth. Catal. 2010, 352, 1851
60. T.-L. Liu, Z.-Y. Xue, H.-Y. Tao, C.-J. Wang, Org. Biomol. Chem. 2011, 9, 1980
61. T.-L. Liu, Z.-L. He, H.-Y. Tao, Y.-P. Cai, C.-J. Wang, Chem. Commun. 2011, 47, 2616
62. H.-L. Teng, H. Huang, H.-Y. Tao, C.-J. Wang, Chem. Commun. 2011, 47, 5494.
63. Quaternary Stereocenters: Challenges and Solution for Organic Synthesis (Eds.:, J. Christoffers, A. Baro,), Wiley-VCH, Weinheim, 2005.