Photocatalytic aerobic oxidation/semipinacol rearrangement sequence: A concise route to the core of pseudoindoxyl alkaloids

Tetrahedron Letters

Volumn 55, Issue 33, 2014, Pages 4648-4652

  Ding, Wei ^a   Zhou, Quan Quan ^a   Xuan, Jun ^a   Li, Tian Ren ^a   Lu, Liang Qiu ^a   Xiao, Wen Jing ^a,b  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b Collaborative Innovation Center of Chemical Science and Engineering ^*  (China)

Author keywords

2,2 Disubstituted indolin 3 one; Aerobic oxidation; Photocatalysis; Semipinacol rearrangement

Indexed keywords

ALKALOID DERIVATIVE; CARBONYL DERIVATIVE; INDOLE DERIVATIVE; IRIDIUM; OXYGEN; RUTHENIUM;

ARTICLE; CYCLIC POTENTIOMETRY; DRUG STRUCTURE; ELECTRON; ENANTIOSELECTIVITY; GREEN CHEMISTRY; HUMAN; LIGHT; OXIDATION; PHOTOCATALYSIS; REACTION ANALYSIS; REACTION TIME;

EID: 84908142721     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.06.102     Document Type: Article

References (59)

1. For some selected examples, see: A.J. Hutchison, and Y. Kishi J. Am. Chem. Soc. 101 1979 6786 6788
2. R.M. Williams, T. Glinka, E. Kwast, H. Coffman, and J.K. Stille J. Am. Chem. Soc. 112 1990 808 821
3. D. Stoermer, and C.H. Heathcock J. Org. Chem. 58 1993 564 568
4. D.L. Boger, J.A. McKie, T. Nishi, and T. Ogiku J. Am. Chem. Soc. 118 1996 2301 2302
5. P.S. Baran, and E.J. Corey J. Am. Chem. Soc. 124 2002 7904 7905
6. L.A. Adams, M.W.N. Valente, and R.M. Williams Tetrahedron 62 2006 5195 5200
7. For selected examples, see: B. Witkop J. Am. Chem. Soc. 72 1950 614 620
8. M. Colonna, L. Greci, and M. Poloni J. Chem. Soc., Perkin Trans. 2 1984 165 169
9. M. Ihara, K. Noguchi, K. Fukumoto, and T. Kametani Tetrahedron 41 1985 2109 2114
10. X. Zhang, and C.S. Foote J. Am. Chem. Soc. 115 1993 8867 8868
11. Y. Liu, and W.W. McWhorter J. Org. Chem. 68 2003 2618 2622
12. Y. Liu, and W.W. McWhorter J. Am. Chem. Soc. 125 2003 4240 4252
13. M. Movassaghi, M.A. Schmidt, and J.A. Ashenhurst Org. Lett. 10 2008 4009 4012
14. K. Higuchi, Y. Sato, S. Kojima, M. Tsuchimochi, K. Sugiura, M. Hatori, and T. Kawasaki Tetrahedron 66 2010 1236 1243
15. Q. Yin, and S.-L. You Chem. Sci. 2 2011 1344 1348
16. Y.-Z. Liu, R.-L. Cheng, and P.-F. Xu J. Org. Chem. 76 2011 2884 2887
17. W. Sun, L. Hong, and R. Wang Chem. Eur. J. 17 2011 6030 6033
18. A. Wetzel, and F. Gagosz Angew. Chem., Int. Ed. 50 2011 7354 7358
19. F. Kolundzic, M.N. Noshi, M. Tjandra, M. Movassaghi, and S.J. Miller J. Am. Chem. Soc. 133 2011 9104 9111
20. M. Rueping, R. Rasappan, and S. Raja Helv. Chim. Acta 95 2012 2296 2303
21. R. Dalpozzo, G. Bartoli, and G. Bencivenni Chem. Soc. Rev. 41 2012 7247 7290
22. For related reviews for the semipinacol rearrangement of α-hydroxyl ketones (also named alpha-ketol rearrangement) L.A. Paquette, and J.E. Hofferberth Org. React. 62 2003 477 567
23. Z.-L. Song, C.-A. Fan, and Y.-Q. Tu Chem. Rev. 111 2011 7523 7556
24. For selected reviews on oxidative reactions with molecular oxygen S.S. Stahl Angew. Chem., Int. Ed. 43 2004 3400 3420
25. T. Mallat, and A. Baiker Chem. Rev. 104 2004 3037 3058
26. T. Punniyamurthy, S. Velusamy, and J. Iqbal Chem. Rev. 105 2005 2329 2363
27. J. Piera, and J.E. Backvall Angew. Chem., Int. Ed. 47 2008 3506 3523
28. Z. Shi, C. Zhang, C. Tang, and N. Jiao Chem. Soc. Rev. 41 2012 3381 3430
29. For selected reviews, see: D. Ravelli, D. Dondi, M. Fagnoni, and A. Albini Chem. Soc. Rev. 38 2009 1999 2011
30. J.M. Narayanam, and C.R. Stephenson Chem. Soc. Rev. 40 2011 102 113
31. F. Teplý Collect. Czech. Chem. Commun. 76 2011 859 917
32. L. Shi, and W. Xia Chem. Soc. Rev. 41 2012 7687 7697
33. J. Xuan, and W.J. Xiao Angew. Chem., Int. Ed. 51 2012 6828 6838
34. D.P. Hari, and B. Konig Angew. Chem., Int. Ed. 52 2013 4734 4743
35. C.K. Prier, D.A. Rankic, and D.W. MacMillan Chem. Rev. 113 2013 5322 5363
36. J. Xuan, L.-Q. Lu, J.-R. Chen, and W.-J. Xiao Eur. J. Org. Chem. 2013 2013 6755 6770
37. M.N. Hopkinson, B. Sahoo, J.-L. Li, and F. Glorius Chem. Eur. J. 20 2014 3874 3886
38. D.M. Schultz, and T.P. Yoon Science 343 2014 985 993
39. For selected examples on visible-light-induced oxidation reactions using oxygen as oxidant: J.M. Zen, S.L. Liou, A.S. Kumar, and M.S. Hsia Angew. Chem., Int. Ed. 42 2003 577 579
40. Y. Su, L. Zhang, and N. Jiao Org. Lett. 13 2011 2168 2171
41. Y.-Q. Zou, J.-R. Chen, X.-P. Liu, L.-Q. Lu, R.L. Davis, K.A. Jorgensen, and W.-J. Xiao Angew. Chem., Int. Ed. 51 2012 784 788
42. X.-Y. Gu, X. Li, Y.-H. Chai, Q. Yang, P.-X. Li, and Y.-M. Yao Green Chem. 15 2013 357 361
43. H. Sun, C. Yang, F. Gao, Z. Li, and W. Xia Org. Lett. 15 2013 624 627
44. S. Zhu, A. Das, L. Bui, H. Zhou, D.P. Curran, and M. Rueping J. Am. Chem. Soc. 135 2013 1823 1829
45. J. An, Y.-Q. Zou, Q.-Q. Yang, Q. Wang, and W.-J. Xiao Adv. Synth. Catal. 355 2013 1483 1489
46. Z. Yuan, S. Zheng, Y. Zeng, J. Chen, Y. Han, and Y. Li New J. Chem. 34 2010 718 722
47. T. Anju, N. Manoj, J.L. Gejo, A.M. Braun, and E. Oliveros Photochem. Photobiol. Sci. 13 2014 281 292
48. Y.-Q. Zou, L.-Q. Lu, L. Fu, N.-J. Chang, J. Rong, J.-R. Chen, and W.-J. Xiao Angew. Chem., Int. Ed. 50 2011 7171 7175
49. B. Trost Science 254 1991 1471 1477
50. P.A. Wender, V.A. Verma, T.J. Paxton, and T.H. Pillow Acc. Chem. Res. 41 2008 40 49
51. P.S. Baran, and R.W. Hoffmann Angew. Chem., Int. Ed. 48 2009 2854 2867
52. CCDC 974938 (2t) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
53. M. Nakagawa, K. Yoshikawa, and T. Hino J. Am. Chem. Soc. 97 1975 6496 6501
54. H. Fujii, R. Ogawa, K. Ohata, T. Nemoto, M. Nakajima, K. Hasebe, H. Mochizuki, and H. Nagase Bioorg. Med. Chem. 17 2009 5983 5988
55. M. Lian, Z. Li, Y. Cai, Q. Meng, and Z. Gao Chem.-Asian J. 7 2012 2019 2023
56. A.A. Frimer Chem. Rev. 79 1979 359 387
57. E.A. Lissi, M.V. Encinas, E. Lemp, and M.A. Rubio Chem. Rev. 93 1993 699 723
58. M. DeRosa, and R.J. Crutchley Coord. Chem. Rev. 233-234 2002 351 371
59. C.-X. Zhuo, W. Zhang, and S.-L. You Angew. Chem., Int. Ed. 51 2012 12662 12686