Bifunctional AgOAc/ThioClickFerrophos complex-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with aryl- and alkylidene malonates

Tetrahedron Letters

Volumn 55, Issue 7, 2014, Pages 1306-1309

  Watanabe, Sayo ^a   Tada, Atsuo ^a   Tokoro, Yuichiro ^a   Fukuzawa, Shin Ichi ^a  

^a CHUO UNIVERSITY   (Japan)

Author keywords

Alkylidene malonate; Azomethine ylide; Chiral phosphine; Cycloaddition; Ferrocene ligand

Indexed keywords

ALKYLIDENE MALONATE DERIVATIVE; ARYLIDENE MALONATE DERIVATIVE; AZOMETHINE YLIDE; ESTER; ESTER DERIVATIVE; GLYCINE; MALONIC ACID DERIVATIVE; PROLINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CYCLOADDITION; ENANTIOSELECTIVITY; PRECURSOR;

EID: 84893720767     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.12.101     Document Type: Article

References (49)

1. W. Zhang Chem. Lett. 42 2013 676 681
2. A.J. Adrio, and J.C. Carretero Chem. Commun. 2011 6784 6794
3. G. Pandy, P. Banerjee, and S.R. Garde Chem. Rev. 106 2006 4484 4517
4. C. Nájera, and J.M. Sansano Angew. Chem., Int. Ed. 44 2005 6272 6276
5. S. Ayana, Ö. Dogana, P.M. Ivantcovab, Nikita G. Datsukb, D.A. Shulgab, V.I. Chupakhinb, D.V. Zabolotnevb, and K.V. Kudryavtsevb Tetrahedron: Asymmetry 24 2013 838 843
6. S.U. Maheswaria, K. Balamurugana, S. Perumala, P. Yogeeswarib, and D. Sriramb Bioorg. Med. Chem. Lett. 20 2010 7278 7282
7. C. Nájera, and J.M. Sansano Org. Biomol. Chem. 7 2009 4567 4581
8. C. Nájera, M. de Gracia Retamosa, J.M. Sansano, A. de Cózar, and F.P. Cossío Eur. J. Org. Chem. 2007 5038 5049
9. J.M. Longmire, B. Wang, and X. Zhang J. Am. Chem. Soc. 124 2002 13400
10. For selected examples in recent five years, L.M. Castelló, C. Nájera, J.M. Sansano, O. Larrañaga, A. de Cózar, and F.P. Cossío Org. Lett. 15 2013 2902 2905
11. S.N. Singh, S. Regati, A.K. Paul, M. Layek, S. Jayaprakash, K.V. Reddy, G.S. Deora, S. Mukherjee, and M. Pal Tetrahedron Lett. 54 2013 5448 5452
12. D. Yan, Q. Li, and C. Wang Chin. J. Chem. 30 2012 2714 2720
13. M. Wang, C.-J. Wang, and Z. Lin Organometallics 31 2012 7870 7876
14. C. Zhang, S.-B. Yu, X.-P. Hu, D.-Y. Wang, and Z. Zheng Org. Lett. 12 2010 5542 5545
15. Q.-H. Li, Z.-Y. Xue, H.-Y. Tao, and C.-J. Wang Tetrahedron Lett. 53 2012 3650 3653
16. R. Robles-Machín, A. López-Pérez, M. González-Esguevillas, J. Adrio, and J.C. Carretero Chem.-Eur. J. 16 2010 9864 9873
17. R. Robles-Machín, M. González-Esguevillas, J. Adrio, and J.C. Carretero J. Org. Chem. 75 2010 233 236
18. J. Hernández-Toribio, R.G. Arrayás, B. Martín- Matute, and J.C. Carretero Org. Lett. 11 2009 393 396
19. A. López-Pérez, J. Adrio, and J.C. Carretero Angew. Chem., Int. Ed. 48 2009 340 343
20. A. López-Pérez, J. Adrio, and J.C. Carretero J. Am. Chem. Soc. 130 2008 10084 10085
21. C.-J. Wang, G. Liang, Z.-Y. Xue, and F. Gao J. Am. Chem. Soc. 130 2008 17250 17251
22. S.-i. Fukuzawa, and H. Oki Org. Lett. 10 2008 1747 1750
23. For selected examples in recent five years, J. Mancebo-Aracil, M. Martín-Rodríguez, C. Nájera, J.M. Sansano, P.R.R. Costa, E.C. de Lima, and A.G. Dias Tetrahedron: Asymmetry 23 2012 1596 1606
24. Y. Yamashita, T. Imaizumi, and S. Kobayashi Angew. Chem., Int. Ed. 50 2011 4893 4896
25. A. López-Pérez, M. Segler, J. Adrio, and J.C. Carretero J. Org. Chem. 76 2011 1945 1948
26. T.-L. Liu, Z.-L. He, A.-H. Li, H.-Y. Tao, and C.-J. Wang Adv. Synth. Catal. 353 2011 1713 1719
27. Y. Yamashita, X.-X. Guo, R. Takashita, and S. Kobayashi J. Am. Chem. Soc. 132 2010 3262 3263
28. I. Oura, K. Shimizu, K. Ogata, and S.-i. Fukuzawa Org. Lett. 12 2010 1752 1755
29. S. Eröksüz, Ö. Dogan, and P.P. Garner Tetrahedron: Asymmetry 21 2010 2535 2541
30. K. Shimizu, K. Ogata, and S.-i. Fukuzawa Tetrahedron Lett. 51 2010 5068 5070
31. H. Xie, J. Zhu, Z. Chen, S. Li, and Y. Wu J. Org. Chem. 75 2010 7468 7471
32. G. Liang, M.-C. Tong, and C.-J. Wang Adv. Synth. Catal. 351 2009 3101 3106
33. C. Nájera, M. de Gracia Retamosa, M. Martín- Rodríguez, J.M. Sansano, A. de Cózar, and F.P. Cossío Eur. J. Org. Chem. 2009 5622 5634
34. C. Nájera, M. de Gracia Retamosa, J.N. Sansano, A. de Cózar, and F.P. Cossío Tetrahedron: Asymmetry 19 2008 2913 2923
35. R. Grigg, C. Kilner, M.A.B. Sarker, C.O. de la Cierva, and H.A. Dondas Tetrahedron 64 2008 8974 8991
36. C. Carmen Nájera, M. de Gracia Retamosa, and J.M. Sansano Angew. Chem., Int. Ed. 47 2008 6055 6058
37. J. Hernández-Toribio, R.G. Arrayás, and J.C. Carretero Chem. Eur. J. 17 2011 6334 6337
38. M. Wang, Y.-H. Shi, J.-F. Luo, W. Du, X.-X. Shi, J.S. Fossey, and W.-P. Deng Catal. Sci. Technol. 1 2011 100 103
39. X. Hou, Q. Li, Y. Jun, and L. Dai Chin. J. Chem. 28 2010 1761 1764
40. L. Liu, R. Sarkisian, Z. Xu, and H. Wang J. Org. Chem. 77 2012 7693 7699
41. R. Viswanatham, C.R. Smith, E.N. Prabhakaran, and J.N. Johnston J. Org. Chem. 2008 3040 3046
42. A.M. Dumas, and E. Fillion Acc. Chem. Res. 43 2010 440 454
43. A. Alexakis, J.E. Bäckvall, O. Pàmies, and M. Diéguez Chem. Rev. 108 2008 2796 2823
44. A. Salomon, V. Capriati, S. Florio, and R. Luisi Org. Lett. 10 2008 1947 1950
45. Z.-Y. Xue, T.-L. Liu, L. Zhou, H. Huang, H.-Y. Hai-Yan Tao, and C.-J. Wang Chem. Commun. 2010 1727 1729
46. M. Wang, Z. Wang, Y.-H. Shi, X.-X. Shi, J.S. Fossey, and W.-P. Deng Angew. Chem., Int. Ed. 50 2011 4897 4900
47. T. Konno, S. Watanabe, T. Takahashi, Y. Tokoro, and S.-i. Fukuzawa Org. Lett. 15 2013 4418 4421
48. For a review of AgOAc bifunctional catalysis (base-free conditions), Q.-A. Chen, D.-S. Wang, and Y.-G. Zhou Chem. Commun. 2010 4043-3051
49. For an example for gold bifunctional catalyst in 1,3-dipolar cycloaddition, M. Martín-Rodríguez, C. Nájera, J.M. Sansano, and F.-L. Wu Tetrahedron: Asymmetry 21 2010 1184 1186