Asymmetric formal [3+2] cycloaddition reaction of α-aryl isocyanoesters with N-aryl maleimides by bifunctional cinchona alkaloids-based squaramide/AgSbF6 cooperative catalysis

Chemistry - An Asian Journal

Volumn 7, Issue 12, 2012, Pages 2777-2781

  Zhao, Mei Xin ^a   Wei, Deng Ke ^a   Ji, Fei Hu ^a   Zhao, Xiao Li ^b   Shi, Min ^a,c  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

3+2 cycloaddition; cooperative catalysis; isocyanoacetates; maleimides; synthetic methods

Indexed keywords

BIFUNCTIONAL; COOPERATIVE CATALYSIS; CYCLOADDITION REACTION; DIASTEREOSELECTIVITIES; ENANTIOSELECTIVE; HIGH YIELD; ISOCYANOACETATES; MALEIMIDES; MILD REACTION CONDITIONS; OPTICALLY ACTIVE; PYRROLE DERIVATIVES; SYNTHETIC METHODS;

CYCLOADDITION; ENANTIOSELECTIVITY; METABOLITES; NITROGEN COMPOUNDS;

CATALYSIS;

EID: 84870284062     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201200686     Document Type: Article

References (59)

1. J.-A. Ma, D. Cahard, Angew. Chem. 2004, 116, 4666-4683
2. Angew. Chem. Int. Ed. 2004, 43, 4566-4583
3. M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491-1508
4. M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Pure Appl. Chem. 2005, 77, 2047-2052
5. Y. J. Park, J.-W. Park, C.-H. Jun, Acc. Chem. Res. 2008, 41, 222-234
6. D. H. Paull, C. J. Abraham, M. T. Scerba, E. Alden-Danforth, T. Lectka, Acc. Chem. Res. 2008, 41, 655-663
7. Z. Shao, H. Zhang, Chem. Soc. Rev. 2009, 38, 2745-2755
8. J. Zhou, Chem. Asian J. 2010, 5, 422-434
9. A. S. K. Hashmi, C. Hubbert, Angew. Chem. 2010, 122, 1026-1028
10. Angew. Chem. Int. Ed. 2010, 49, 1010-1012
11. C. Zhong, X. Shi, Eur. J. Org. Chem. 2010, 2999-3025
12. A. E. Allen, D. W. C. MacMillan, Chem. Sci. 2012, 3, 633-658
13. L. Stegbauer, F. Sladojevich, D. J. Dixon, Chem. Sci. 2012, 3, 942-958.
14. J. Alemán, A. Parra, H. Jiang, K. A. Jørgensen, Chem. Eur. J. 2011, 17, 6890-6899; For selected recent examples, see
15. Y.-F. Wang, R.-X. Chen, K. Wang, B.-B. Zhang, Z.-B. Li, D.-Q. Xu, Green Chem. 2012, 14, 893-895
16. J.-B. Ling, Y. Su, H.-L. Zhu, G.-Y. Wang, P.-F. Xu, Org. Lett. 2012, 14, 1090-1093
17. X. Wang, W. Yao, Z. Yao, C. Ma, J. Org. Chem. 2012, 77, 2959-2965
18. H.-J. Yang, L. Dai, S.-Q. Yang, F.-E. Chen, Synlett 2012, 948-950
19. J.-Y. Qian, C.-C. Wang, F. Sha, X.-Y. Wu, RSC Adv. 2012, 2, 6042-6048
20. W. Yang, D.-M. Du, Chem. Commun. 2011, 47, 12706-12708
21. N. Hara, S. Nakamura, Y. Funahashi, N. Shibata, Adv. Synth. Catal. 2011, 353, 2976-2980
22. C. Min, X. Han, Z. Liao, X. Wu, H.-B. Zhou, C. Dong, Adv. Synth. Catal. 2011, 353, 2715-2720
23. V. Marcos, J. Aleman, J. L. Garcia Ruano, F. Marini, M. Tiecco, Org. Lett. 2011, 13, 3052-3055
24. J. P. Malerich, K. Hagihara, V. H. Rawal, J. Am. Chem. Soc. 2008, 130, 14416-14417.
25. A. V. Lygin, A. de Meijere, Angew. Chem. 2010, 122, 9280-9311
26. Angew. Chem. Int. Ed. 2010, 49, 9094-9124
27. A. V. Gulevich, A. G. Zhdanko, R. V. A. Orru, V. G. Nenajdenko, Chem. Rev. 2010, 110, 5235-5331.
28. Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405-6406
29. Y. Ito, M. Sawamura, T. Hayashi, Tetrahedron Lett. 1987, 28, 6215-6218
30. T. Hayashi, M. Sawamura, Y. Ito, Tetrahedron 1992, 48, 1999-2012
31. T. Hayashi, Y. Uozumi, A. Yamazaki, M. Sawamura, H. Hamashima, Y. Ito, Tetrahedron Lett. 1991, 32, 2799-2802.
32. Y. Ito, M. Sawamura, T. Hayashi, Tetrahedron Lett. 1988, 29, 239-240
33. A. Togni, S. D. Pastor, G. Rihs, Helv. Chim. Acta 1989, 72, 1471-1478
34. M. D. Bachi, A. Melman, J. Org. Chem. 1997, 62, 1896-1898.
35. Y. Ito, M. Sawamura, M. Kobayashi, T. Hayashi, Tetrahedron Lett. 1988, 29, 6321-6324
36. S. D. Pastor, A. Togni, J. Am. Chem. Soc. 1989, 111, 2333-2334
37. A. Togni, S. D. Pastor, Tetrahedron Lett. 1989, 30, 1071-1072
38. M. Sawamura, Y. Ito, T. Hayashi, Tetrahedron Lett. 1989, 30, 2247-2250
39. M. Sawamura, Y. Nakayama, T. Kato, Y. Ito, J. Org. Chem. 1995, 60, 1727-1732.
40. J. M. Longmire, X. Zhang, M. Shang, Organometallics 1998, 17, 4374-4379
41. F. Gorla, A. Togni, L. M. Venanzi, A. Albinati, F. Lianza, Organometallics 1994, 13, 1607-1616
42. Y. Motoyama, H. Kawakami, K. Shimozono, K. Aoki, H. Nishiyama, Organometallics 2002, 21, 3408-3416
43. S. Gosiewska, M. H. in't Vald, J. J. M. de Pater, P. C. A. Bruijnincx, M. Lutz, A. L. Spek, G. van Koten, R. J. M. Klein Gebbink, Tetrahedron: Asymmetry 2006, 17, 674-686
44. S. Gosiewska, S. M. Herreras, M. Lutz, A. L. Spek, R. W. A. Havenith, G. P. M. van Klink, G. van Koten, R. J. M. Klein Gebbink, Organometallics 2008, 27, 2549-2559.
45. C. Guo, M.-X. Xue, M.-K. Zhu, L.-Z. Gong, Angew. Chem. 2008, 120, 3462-3465
46. Angew. Chem. Int. Ed. 2008, 47, 3414-3417.
47. M.-X. Xue, C. Guo, L.-Z. Gong, Synlett 2009, 2191-2197
48. F. Sladojevich, A. Trabocchi, A. Guarna, D. J. Dixon, J. Am. Chem. Soc. 2011, 133, 1710-1713
49. H. Y. Kim, K. Oh, Org. Lett. 2011, 13, 1306-1309.
50. Z.-W. Zhang, G. Lu, M.-M. Chen, N. Lin, Y.-B. Li, T. Hayashi, A. S. C. Chan, Tetrahedron: Asymmetry 2010, 21, 1715-1721
51. S. Nakamura, Y. Maeno, M. Ohara, A. Yamamura, Y. Funahashi, N. Shibata, Org. Lett. 2012, 14, 2960-2963.
52. For recent example on the asymmetric addition to azodicarboxylates, see:, D. Monge, K. L. Jensen, I. Marín, K. A. Jørgensen, Org. Lett. 2011, 13, 328-331.
53. C. Arrõniz, A. Gil-González, V. Semak, C. Escolano, J. Bosch, M. Amat, Eur. J. Org. Chem. 2011, 3755-3760
54. J. Song, C. Guo, P.-H. Chen, J. Yu, S.-W. Luo, L.-Z. Gong, Chem. Eur. J. 2011, 17, 7786-7790
55. L.-L. Wang, J.-F. Bai, L. Peng, L.-W. Qi, L.-N. Jia, Y.-L. Guo, X.-Y. Luo, X. Xu, L.-X. Wang, Chem. Commun. 2012, 48, 5175-5177.
56. J.-F. Bai, L.-L. Wang, L. Peng, Y.-L. Guo, L.-N. Jia, F. Tian, G.-Y. He, X.-Y. Xu, L.-X. Wang, J. Org. Chem. 2012, 77, 2947-2953
57. S. Padilla, J. Adrio, J. C. Carretero, J. Org. Chem. 2012, 77, 4161-4166
58. M.-X. Zhao, D.-K. Wei, T.-L. Dai, F.-H. Ji, H. Zhou, M. Shi, 2012, unpublished results.
59. R. Grigg, M. I. Lansdell, M. Thornton-Pett, Tetrahedron 1999, 55, 2025-2044.