Asymmetric [3 + 2] Cycloaddition of Methyleneindolinones with N,N′-Cyclic Azomethine Imines Catalyzed by a N,N′-Dioxide-Mg(OTf)2 Complex

Journal of Organic Chemistry

Volumn 80, Issue 19, 2015, Pages 9691-9699

  Yin, Chengkai ^a   Lin, Lili ^a   Zhang, Dong ^a   Feng, Juhua ^a   Liu, Xiaohua ^a   Feng, Xiaoming ^a,b  

^a Sichuan University   (China)

^b SynBio Research Platform   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUNDS;

1 ,3-DIPOLARCYCLOADDITION; AZOMETHINE; CATALYST SYSTEM; METHYLENEINDOLINONES; MILD REACTION CONDITIONS; TERTIARY STEREOCENTERS;

NITROGEN COMPOUNDS;

AZOMETHINE YLIDE; CYCLOPENTANE DERIVATIVE; IMINE; INDOLE DERIVATIVE; MAGNESIUM DERIVATIVE; PYRAZOLE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; CYCLOADDITION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 84942941271     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b01760     Document Type: Article

References (66)

1. Padwa, A. and Pearson, W. H. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Wiley: New York, 2003; Vol. 59.
2. Hashimoto, T. and Maruoka, K. In Handbook of Cyclization Reactions; Ma, S., Ed.; Wiley-VCH: Weinheim, Germany, 2009; Ch. 3, p 87.
3. Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887 10.1021/cr078371m
4. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863 10.1021/cr970324e
5. Hashimoto, T.; Maruoka, K. Chem. Rev. 2015, 115, 5366 10.1021/cr5007182
6. Gothelf, K. V.; Jørgensen, K. A. Chem. Commun. 2000, 1449 10.1039/b004597g
7. Murahashi, S.-I.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J. Org. Chem. 1990, 55, 1736 10.1021/jo00293a013
8. Nájera, C.; Sansano, J. M. Curr. Org. Chem. 2003, 7, 1105 10.2174/1385272033486594
9. Nájera, C.; Sansano, J. M. Angew. Chem., Int. Ed. 2005, 44, 6272 10.1002/anie.200501074
10. Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765 10.1021/cr040004c
11. Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484 10.1021/cr050011g
12. Adrio, J.; Carretero, J. C. Chem. Commun. 2014, 50, 12434 10.1039/C4CC04381B
13. Sibi, M. P.; Stanley, L. M.; Jasperse, C. P. J. Am. Chem. Soc. 2005, 127, 8276 10.1021/ja051650b
14. Sibi, M. P.; Stanley, L. M.; Soeta, T. Adv. Synth. Catal. 2006, 348, 2371 10.1002/adsc.200600307
15. Liu, K. C.; Shelton, B. R.; Howe, R. K. J. Org. Chem. 1980, 45, 3916 10.1021/jo01307a039
16. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339 10.1021/ja01505a017
17. Grundmann, C.; Dean, J. M. J. Org. Chem. 1965, 30, 2809 10.1021/jo01019a074
18. Sibi, M. P.; Itoh, K.; Jasperse, C. P. J. Am. Chem. Soc. 2004, 126, 5366 10.1021/ja0318636
19. Dorn, H.; Otto, A. Angew. Chem., Int. Ed. Engl. 1968, 7, 214 10.1002/anie.196802141
20. Dorn, H.; Otto, A. Chem. Ber. 1968, 101, 3287 10.1002/cber.19681010936
21. Karlsson, S.; Högberg, H.-E. Org. Prep. Proced. Int. 2001, 33, 103 10.1080/00304940109356583
22. Stanovnik, B.; Jelin, B.; Turk, C.; Zlicer, M.; Svete, J. J. Heterocycl. Chem. 1998, 35, 1187 10.1002/jhet.5570350514
23. Qiu, G.; Kuang, Y.; Wu, J. Adv. Synth. Catal. 2014, 356, 3483 10.1002/adsc.201400631
24. Ogawa, S.; Nishimine, T.; Tokunaga, E.; Shibata, N. Synthesis 2010, 2010, 3274 10.1055/s-0030-1258189
25. Koptelov, Y. B.; Sednev, M. V. Russ. J. Org. Chem. 2011, 47, 547 10.1134/S1070428011040130
26. Pezdirc, L.; Bevk, D.; Grošelj, U.; Meden, A.; Stanovnik, B.; Svete, J. J. Comb. Chem. 2007, 9, 717 10.1021/cc070041s
27. Pezdirc, L.; Jovanovski, V.; Bevk, D.; Jakše, R.; Pirc, S.; Meden, A.; Stanovnik, B.; Svete, J. Tetrahedron 2005, 61, 3977 10.1016/j.tet.2005.02.049
28. Shintani, R.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 10778 10.1021/ja036922u
29. Suárez, A.; Downey, C. W.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 11244 10.1021/ja052876h
30. Hashimoto, T.; Maeda, Y.; Omote, M.; Nakatsu, H.; Maruoka, K. J. Am. Chem. Soc. 2010, 132, 4076 10.1021/ja100787a
31. Kato, T.; Fujinami, S.; Ukaji, Y.; Inomata, K. Chem. Lett. 2008, 37, 342 10.1246/cl.2008.342
32. Tanaka, K.; Kato, T.; Fujinami, S.; Ukaji, Y.; Inomata, K. Chem. Lett. 2010, 39, 1036 10.1246/cl.2010.1036
33. Chen, W.; Yuan, X.-H.; Li, R.; Du, W.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Adv. Synth. Catal. 2006, 348, 1818 10.1002/adsc.200606102
34. Chen, W.; Du, W.; Duan, Y.-Z.; Wu, Y.; Yang, S.-Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2007, 46, 7667 10.1002/anie.200702618
35. Hashimoto, T.; Omote, M.; Maruoka, K. Angew. Chem., Int. Ed. 2011, 50, 3489 10.1002/anie.201100331
36. Hong, L.; Kai, M.; Wu, C. Y.; Sun, W. S.; Zhu, G. M.; Li, G. F.; Yao, X. J.; Wang, R. Chem. Commun. 2013, 49, 6713 10.1039/c3cc41507d
37. Hori, M.; Sakakura, A.; Ishihara, K. J. Am. Chem. Soc. 2014, 136, 13198 10.1021/ja508441t
38. Imaizumi, T.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2012, 134, 20049 10.1021/ja311150n
39. Arai, T.; Ogino, Y. Molecules 2012, 17, 6170 10.3390/molecules17056170
40. Chen, X.-H.; Wei, Q.; Luo, S.-W.; Xiao, H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 13819 10.1021/ja905302f
41. Antonchick, A. P.; Gerding- Reimers, C.; Catarinella, M.; Schürmann, M.; Preut, H.; Ziegler, S.; Rauh, D.; Waldmann, H. Nat. Chem. 2010, 2, 735 10.1038/nchem.730
42. Tan, B.; Candeias, N. R.; Barbas, C. F., III Nat. Chem. 2011, 3, 473 10.1038/nchem.1039
43. Tan, B.; Candeias, N. R.; Barbas, C. F., III J. Am. Chem. Soc. 2011, 133, 4672 10.1021/ja110147w
44. Jiang, X.; Cao, Y.; Wang, Y.; Liu, L.; Shen, F.; Wang, R. J. Am. Chem. Soc. 2010, 132, 15328 10.1021/ja106349m
45. Hong, L.; Wang, R. Adv. Synth. Catal. 2013, 355, 1023 10.1002/adsc.201200808
46. Williams, R. M.; Cox, R. J. Acc. Chem. Res. 2003, 36, 127 10.1021/ar020229e
47. Lin, H.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 36 10.1002/anie.200390048
48. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748 10.1002/anie.200701342
49. Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000; p 59.
50. The Chemistry of Organomagnesium Compounds; Rappoport, Z.; Marek, I., Eds.; Wiley: New York, 2008; Part 1.
51. Eisch, J. J. Organometallics 2002, 21, 5439 10.1021/om0109408
52. Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302 10.1002/anie.200300579
53. Hoffmann, R. W. Chem. Soc. Rev. 2003, 32, 225 10.1039/b300840c
54. Satoh, T. Chem. Soc. Rev. 2007, 36, 1561 10.1039/b615630b
55. Kobayashi, S.; Yamashita, Y. Acc. Chem. Res. 2011, 44, 58 10.1021/ar100101b
56. Yamashita, Y.; Tsubogo, T.; Kobayashi, S. Chem. Sci. 2012, 3, 967 10.1039/C1SC00744K
57. Kanemasa, S.; Nishiuchi, M.; Kamimura, A.; Hori, K. J. Am. Chem. Soc. 1994, 116, 2324 10.1021/ja00085a012
58. Saito, S.; Tsubogo, T.; Kobayashi, S. J. Am. Chem. Soc. 2007, 129, 5364 10.1021/ja0709730
59. Tsubogo, T.; Saito, S.; Seki, K.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2008, 130, 13321 10.1021/ja8032058
60. Liu, X. H.; Lin, L. L.; Feng, X. M. Acc. Chem. Res. 2011, 44, 574 10.1021/ar200015s
61. Liu, X. H.; Lin, L. L.; Feng, X. M. Org. Chem. Front. 2014, 1, 298 10.1039/c3qo00059a
62. Shen, K.; Liu, X. H.; Lin, L. L.; Feng, X. M. Chem. Sci. 2012, 3, 327 10.1039/C1SC00544H
63. Zheng, K.; Yin, C. K.; Liu, X. H.; Lin, L. L.; Feng, X. M. Angew. Chem., Int. Ed. 2011, 50, 2573 10.1002/anie.201007145
64. Yin, C. K.; Cao, W. D.; Lin, L. L.; Liu, X. H.; Feng, X. M. Adv. Synth. Catal. 2013, 355, 1924 10.1002/adsc.201300335
65. Zheng, J. F.; Lin, L. L.; Kuang, Y. L.; Zhao, J. N.; Liu, X. H.; Feng, X. M. Chem. Commun. 2014, 50, 994 10.1039/C3CC47800A
66. CCDC 1055204 (3t). For more data see Supporting Information.