Enantioselective Synthesis of Dihydropyran-Fused Indoles through [4+2] Cycloaddition between Allenoates and 3-Olefinic Oxindoles

Journal of Organic Chemistry

Volumn 80, Issue 10, 2015, Pages 5279-5286

  Wang, Feng ^a   Li, Zhen ^a   Wang, Jie ^a   Li, Xin ^a   Cheng, Jin Pei ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

POLYOLS; STEREOCHEMISTRY;

CHEMICAL EQUATIONS; CYCLOADDITION PRODUCTS; DIHYDROPYRAN; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; HIGH YIELD; LEWIS BASE;

ENANTIOSELECTIVITY;

INDOLE DERIVATIVE; LEWIS BASE; OXINDOLE; ALKENE; PYRAN DERIVATIVE; SPIRO COMPOUND;

ANNULATION REACTION; ARTICLE; CATALYST; CHIRALITY; CYCLIZATION; CYCLOADDITION; ENANTIOMER; ENANTIOSELECTIVITY; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALKENES; CATALYSIS; CYCLOADDITION REACTION; INDOLES; LEWIS BASES; PYRANS; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84929598167     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00212     Document Type: Article

References (60)

1. Wright, C. W.; Allen, D.; Cai, Y.; Phillipson, J. D. Phytother. Res. 1992, 6, 121
2. Kam, T. S.; Tan, S. J.; Ng, S. W.; Kmiyama, K. Org. Lett. 2008, 10, 3749
3. Beniddir, M. A.; Martin, M.-T.; Huu Dau Tran, M.-E.; Grellier, P.; Rasoanaivo, P.; Guéritte, F.; Litaudon, M. Org. Lett. 2012, 14, 4162
4. Sakakibara, T.; Karasumaru, S.; Kawano, I. J. Am. Chem. Soc. 1985, 107, 6417
5. Feldman, K. S.; Karatjas, A. G. Org. Lett. 2004, 6, 2849
6. Reh, S.; Bergman, J. Tetrahedron 2005, 61, 3115
7. Feldman, K. S.; Vidulova, D. B.; Karatjas, A. D. J. Org. Chem. 2005, 70, 6429
8. Miyamoto, H.; Okawa, Y.; Nakazaki, A.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45, 2274
9. Boal, B. W.; Schammel, A. W.; Garg, N. K. Org. Lett. 2009, 11, 3458
10. Schammel, A. W.; Boal, B. W.; Zu, L.; Mesganaw, T.; Garg, N. K. Tetrahedron 2010, 66, 4687
11. Zhang, X.; Yang, Z.-P.; Liu, C.; You, S.-L. Chem. Sci. 2013, 4, 3239
12. Lv, H.; Chen, X.-Y.; Sun, L.-h.; Ye, S. J. Org. Chem. 2010, 75, 6973
13. Yang, L.; Wang, F.; Chua, P. J.; Lv, Y.; Zhong, L.-J.; Zhong, G. Org. Lett. 2012, 14, 2894
14. Mao, Z.; Li, W.; Shi, Y.; Mao, H.; Lin, A.; Zhu, C.; Cheng, Y. Chem.-Eur. J. 2013, 19, 9754
15. Lang, R. W.; Hansen, H.-J. Org. Synth. 1984, 62, 202
16. Lu, H.; Leow, D.; Huang, K.-W.; Tan, C.-H. J. Am. Chem. Soc. 2009, 131, 7212
17. Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906
18. Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535
19. Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035
20. Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140
21. Cowen, B. J.; Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102
22. Marinetti, A.; Voituriez, A. Synlett 2010, 174
23. Wei, Y.; Shi, M. Acc. Chem. Res. 2010, 43, 1005
24. López, F.; Mascareñas, J. L. Chem.-Eur. J. 2011, 17, 418
25. Zhao, Q.-Y.; Lian, Z.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 1724
26. Fan, Y. C.; Kwon, O. Chem. Commun. 2013, 49, 11588
27. Wang, Z.; Xu, X.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927
28. Atta-ur-Rahman; Nasreen, A.; Akhtar, F.; Shekhani, M. S.; Clardy, J.; Parvez, M.; Choudhary, M. I. J. Nat. Prod. 1997, 60, 472
29. Yang, W.; Shang, D.; Liu, Y.; Du, Y.; Feng, X. J. Org. Chem. 2005, 70, 8533
30. Smith, A. B.; Sperry, J. B.; Han, Q. J. Org. Chem. 2007, 72, 6891
31. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2009, 131, 14176
32. Canham, S. M.; France, D. J.; Overman, L. E. J. Am. Chem. Soc. 2010, 132, 7876
33. Crimmins, M. T.; Haley, M. W.; Bryan, E. A. O. Org. Lett. 2011, 13, 4712
34. Kobayashi, H.; Kanematsu, M.; Yoshida, M.; Shishido, K. Chem. Commun. 2011, 47, 7440
35. Ramachandran, P. V.; Tafelska-Kaczmarek, A.; Sakavuyi, K.; Chatterjee, A. Org. Lett. 2011, 13, 1302
36. Trost, B. M.; Frontier, A. J.; Thiel, O. R.; Yang, H.; Dong, G. Chem.-Eur. J. 2011, 17, 9762
37. Trost, B. M.; Seganish, W. M.; Chung, C. K.; Amans, D. Chem.-Eur. J. 2012, 18, 2948
38. Conyers, R. C.; Gung, B. W. Chem.-Eur. J. 2013, 19, 654
39. Zhu, X.; Schaffner, A.; Li, R. C.; Kwon, O. Org. Lett. 2005, 7, 2977
40. Creech, G. S.; Kwon, O. Org. Lett. 2008, 10, 429
41. Wang, T.; Ye, S. Org. Lett. 2010, 12, 4168
42. Yao, W.; Dou, X.; Lu, Y. J. Am. Chem. Soc. 2015, 137, 54
43. Wang, X.; Fang, T.; Tong, X. Angew. Chem., Int. Ed. 2011, 50, 5361
44. Ashtekar, K. D.; Staples, R. J.; Borhan, B. Org. Lett. 2011, 13, 5732
45. Pei, C.-K.; Shi, M. Tetrahedron: Asymmetry 2011, 22, 1239
46. Pei, C.-K.; Jiang, Y.; Shi, M. Org. Biomol. Chem. 2012, 10, 4355
47. Pei, C.-K.; Jiang, Y.; Wei, Y.; Shi, M. Angew. Chem., Int. Ed. 2012, 51, 11328
48. Zhao, Q.-Y.; Huang, L.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2012, 354, 1926
49. Takizawa, S.; Arteaga, F. A.; Yoshida, Y.; Suzuki, M.; Sasai, H. Org. Lett. 2013, 15, 4142
50. Chen, X.-Y.; Wen, M.-W.; Ye, S.; Wang, Z.-X. Org. Lett. 2011, 13, 1138
51. Zhang, X.-C.; Cao, S.-H.; Wei, Y.; Shi, M. Org. Lett. 2011, 13, 1142
52. Zhang, D.-H.; Shi, M. ChemistryOpen 2012, 1, 215
53. Yang, H.-B.; Zhao, Y.-Z.; Sang, R.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2014, 356, 3799
54. 3 = H, only trace product was achieved. It is suggested that the protecting groups (especially for the electron-withdrawing groups) are necessary for the reaction.
55. When 4-substituted derivatives of allenoates (e.g., methyl 5-phenylpenta-2,3-dienoate and ethyl penta-2,3-dienoate) were selected as substrates, no [4+2] cycloaddtion products were isolated.
56. CCDC 1057332 and 992745 contain the supplementary crystallographic data for compound 3j and 3t, respectively. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
57. Milanesio, M.; Viterbo, D.; Albini, A.; Fasani, E.; Bianchi, R.; Barzaghi, M. J. Org. Chem. 2000, 65, 3416
58. Chen, X. H.; Wei, Q.; Luo, S. W.; Xiao, H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 13819
59. Tan, B.; Candeias, N. R.; Barbas, C. F., III. J. Am. Chem. Soc. 2011, 133, 4672
60. Buzas, A.; Merour, J. Y. Synthesis 1989, 458