Cu(i)/TF-BiphamPhos-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with dimethyl itaconate and 2-methyleneglutarate

RSC Advances

Volumn 4, Issue 32, 2014, Pages 16899-16905

  Tao, Hai Yan ^a   He, Zhao Lin ^a   Yang, Yang ^a   Wang, Chun Jiang ^a,b  

^a WUHAN UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; AZOMETHINE YLIDES; CATALYTIC SYSTEM; DIASTEREO-SELECTIVITY; DIMETHYL ITACONATE; EFFICIENT CONSTRUCTION; PYRROLIDINE DERIVATIVES; STEREOGENIC CENTERS;

CYCLOADDITION;

EID: 84897986463     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c4ra02195a     Document Type: Article

References (67)

1. S. G. Pyne A. S. Davis N. J. Gates J. Nicole J. P. Hartley K. B. Lindsay T. Machan M. Tang Synlett 2004 2670
2. L. M. Harwood and R. J. Vickers, in Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, ed., A. Padwa, and, W. Pearson, Wiley & Sons, New York, 2002
3. Privileged Chiral Ligands and Catalysts, ed., Q.-L. Zhou, Wiley-VCH, Weinheim, 2011
4. A. Berkessel and H. Gröger, Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weinheim 2004
5. J. Yu F. Shi L.-Z. Gong Acc. Chem. Res. 2011 44 1156
6. J. Adrio J. C. Carretero Chem. Commun. 2011 47 6784
7. B. Engels M. Christl Angew. Chem., Int. Ed. 2009 48 7968
8. L. M. Stanley M. P. Sibi Chem. Rev. 2008 108 2887
9. M. Alvarez-Corral M. Munoz-Dorado I. Rodriguez-Garcia Chem. Rev. 2008 108 3174
10. M. Bonin A. Chauveau L. Micouin Synlett 2006 2349
11. C. Nájera J. M. Sansano Angew. Chem., Int. Ed. 2005 44 6272
12. S. L. Schreiber Science 2000 287 1964
13. C. Chen X. Li S. L. Schreiber J. Am. Chem. Soc. 2003 125 10174
14. J. M. Longmire B. Wang X. Zhang J. Am. Chem. Soc. 2002 124 13400
15. A. S. Gothelf K. V. Gothelf R. G. Hazell K. A. Jørgensen Angew. Chem., Int. Ed. 2002 41 4236
16. A. Awata T. Arai Chem.-Eur. J. 2012 18 8278
17. L. Wang X.-M. Shi W.-P. Dong L.-P. Zhu R. Wang Chem. Commun. 2013 49 3458
18. L. He X.-H. Chen D.-N. Wang S.-W. Luo W.-Q. Zhang J. Yu L. Ren L.-Z. Gong J. Am. Chem. Soc. 2011 133 13504
19. X.-H. Chen W.-Q. Zhang L.-Z. Gong J. Am. Chem. Soc. 2008 130 5652
20. W. Zeng G.-Y. Chen Y.-G. Zhou Y.-X. Li J. Am. Chem. Soc. 2007 129 750
21. W. Zeng Y.-G. Zhou Org. Lett. 2005 7 5055
22. J.-W. Shi M.-X. Zhao Z.-Y. Lei M. Shi J. Org. Chem. 2008 73 305
23. T. Arai A. Mishiro N. Yokoyama K. Suzuli H. Sato J. Am. Chem. Soc. 2010 132 5338
24. C. Nájera M. D. G. Retamosa J. Sansano Angew. Chem., Int. Ed. 2008 47 6055
25. C. Chen X. Li S. L. Schreiber J. Am. Chem. Soc. 2003 125 10174
26. X.-X. Yan Q. Peng Y. Zhang K. Zhang W. Hong X.-L. Hou Y.-D. Wu Angew. Chem., Int. Ed. 2006 45 1979
27. S. Cabrera R. Gómez Arrayás J. C. Carretero J. Am. Chem. Soc. 2005 127 16394
28. S. Saito T. Tsubogo S. Kobayashi J. Am. Chem. Soc. 2007 129 5364
29. Y. Yamashita T. Imaizumi S. Kobayashi Angew. Chem., Int. Ed. 2011 50 4893
30. H. Y. Kim J.-Y. Li S. Kim K. Oh J. Am. Chem. Soc. 2011 133 20750
31. J. Hernández-Toribio S. Padilla J. Adrio J. C. Carretero Angew. Chem., Int. Ed. 2012 51 8854
32. R. Narayan J. O. Bauer C. Strohmann A. P. Antonchick H. Waldmann Angew. Chem., Int. Ed. 2013 52 12892
33. S. Watanabe A. Tada Y. Tokoro S.-i. Fukuzawa Tetrahedron Lett. 2014 55 1306
34. W. Tang X. Zhang Chem. Rev. 2003 103 3029
35. H. U. Blaser C. Malan B. Pugin F. Spindler H. Steiner M. Studer Adv. Synth. Catal. 2003 345 103
36. Y. S. Or, C. Wang, X. Peng, L. Ying and Y.-L. Qiu, US Pat., 20100074863, 2010
37. Quaternary Stereocenters: Challenges and Solution for Organic Synthesis, ed., J. Christoffers, and, A. Baro, WILEY-VCH, Weinheim, 2005
38. B. M. Trost C. Jiang Synthesis 2006 369
39. C.-J. Wang G. Liang Z.-Y. Xue F. Gao J. Am. Chem. Soc. 2008 130 17250
40. C.-J. Wang Z.-Y. Xue G. Liang Z. Lu Chem. Commun. 2009 2905
41. G. Liang M.-C. Tong C.-J. Wang Adv. Synth. Catal. 2009 351 3101
42. Z.-Y. Xue T.-L. Liu Z. Lu H. Huang H.-Y. Tao C.-J. Wang Chem. Commun. 2010 46 1727
43. G. Liang M.-C. Tong H.-Y. Tao C.-J. Wang Adv. Synth. Catal. 2010 352 1851
44. T.-L. Liu Z.-Y. Xue H.-Y. Tao C.-J. Wang Org. Biomol. Chem. 2011 9 1980
45. Z.-Y. Xue X. Fang C.-J. Wang Org. Biomol. Chem. 2011 9 3622
46. T.-L. Liu Z.-L. He H.-Y. Tao C.-J. Wang Chem.-Eur. J. 2012 18 8042
47. T.-L. Liu Z.-L. He H.-Y. Tao Y.-P. Cai C.-J. Wang Chem. Commun. 2011 47 2616
48. Q.-H. Li M.-C. Tong J. Li H.-Y. Tao C.-J. Wang Chem. Commun. 2011 47 11110
49. T.-L. Liu Z.-L. He C.-J. Wang Chem. Commun. 2011 47 9600
50. H.-L. Teng H. Huang H.-Y. Tao C.-J. Wang Chem. Commun. 2011 47 5494
51. H.-L. Teng F.-L. Luo H.-Y. Tao C.-J. Wang Org. Lett. 2011 13 5600
52. T.-L. Liu Z.-L. He Q.-H. Li H.-Y. Tao C.-J. Wang Adv. Synth. Catal. 2011 353 1713
53. M.-C. Tong J. Li H.-Y. Tao Y.-X. Li C.-J. Wang Chem.-Eur. J. 2011 17 12922
54. D. Yan Q. Li C.-J. Wang Chin. J. Chem. 2012 30 2714
55. Q.-H. Li Z.-Y. Xue H.-Y. Tao C.-J. Wang Tetrahedron Lett. 2012 53 3650
56. T.-L. Liu Z.-L. He H.-Y. Tao C.-J. Wang Chem.-Eur. J. 2012 18 8042
57. H.-L. Teng H. Huang C.-J. Wang Chem.-Eur. J. 2012 18 16214
58. K. Liu H.-L. Teng L. Yao H.-Y. Tao C.-J. Wang Org. Lett. 2013 15 2250
59. Z.-L. He H.-L. Teng C.-J. Wang Angew. Chem., Int. Ed. 2013 52 2934
60. H. Y. Kim H.-J. Shih W. E. Knabe K. Oh Angew. Chem., Int. Ed. 2009 48 7420
61. C. Nájera M. D. G. Retamosa J. M. Sansano A. Cózar F. P. Cossío Tetrahedron: Asymmetry 2008 19 2913
62. B. Zhao Z. Han K. L. Ding Angew. Chem., Int. Ed. 2013 53 4744
63. Z.-Y. Xue Q.-H. Li H.-Y. Tao C.-J. Wang J. Am. Chem. Soc. 2011 133 11757
64. M.-C. Tong J. Li H.-Y. Tao Y.-X. Li C.-J. Wang Chem.-Eur. J. 2011 17 12922
65. M. Wang C.-J. Wang Z. Lin Organometallics 2012 31 7870
66. P. Fackler C. Berthold F. Voss T. Bach J. Am. Chem. Soc. 2010 132 15911
67. Z.-C. Duan X.-P. Hu J. Deng S.-B. Yu D.-Y. Wang Z. Zheng Tetrahedron: Asymmetry 2009 20 588