Synthesis of functionalized indoles with an α-stereogenic ketone moiety through an enantioselective friedel-crafts alkylation with (E)-1,4-Diaryl-2-butene-1,4-diones

Advanced Synthesis and Catalysis

Volumn 351, Issue 14-15, 2009, Pages 2433-2440

  Blay, Gonzalo ^a   Fernández, Isabel ^a   Monleón, Alicia ^a   Muñoz, M Carmen ^b   Pedro, José R ^a   Vila, Carlos ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

Asymmetric catalysis; Enones; Hafnium; O ligands; Umpolung, zirconium

Indexed keywords

EID: 70350608159     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900357     Document Type: Article

References (84)

1. For examples of relevant natural products and potential medicinal agents, see : a) R. D. Dillard, N. J. Bach, S. E. Draheim, D. R. Berry, D. G. Carlson, N. Y. Chirgadze, D. K. Clawson, L. W. Hartley, L. M. Johnson, N. D. Jones, E. R. McKinney, E. D. Mihelich, J. L. Olkowski, R. W. Schevitz, A.C. Smith, D.W. Snyder, CD. Sommers, J.-R Wery, J. Med. Chem. 1996, 39, 5119-5136;
2. b) D. M. Leonard, K. R. Shuler, C. J. Poulter, S. R. Eaton, T. K. Sawyer, J. C. Hodges, T.-Z. Su, J. D. Schölten, R. Gowan, S. Judith, J. S. Sebolt-Leopold, A. M. Doherty, J. Med. Chem. 1997, 40, 192-200;
3. c) U Huber, R. E. Moore, G. M. L. Patterson, J. Nat. Prod. 1998, 61, 1304-1306;
4. d) S. K. Rabindran, H. He, M. Singh, E. Brown, K. I. Collins, T. Annable, L. M. Greenberger, Cancer Res. 1998, 58, 5850-5858;
5. e) Rawson, K. N. Dack, R. P. Dickinson, K. D. J. James, Bioorg. Med. Chem. Lett. 2002, 12, 125-128;
6. f) T. Nickelsen, A. Samel, M. Vejvoda, J. Wenzel, B. Smith, R. Gerzer, Chronobiol. Int. 2002, 19, 915-936;
7. g) I. Mancini, G. Guella, H. Zibrowius, F. Pietra, Tetrahedron 2003, 59, 8757-8762;
8. h) T. Kam, Y. Choo, J. Nat. Prod. 2004, 67, 547-552;
9. i) A. C. Kinsman, M. A. Kerr, J. Am. Chem. Soc. 2003, 125, 14120-14125;
10. j) J. ChangFong, J. B. Rangisetty, M. Dukat, V. Setola, T. Raffay, B. Roth, R. Glennon, Bioorg. Med. Chem. Lett. 2004, 14, 1961-1964;
11. k) J. Croonenberghs, A. Wauters, D. Deboutte, R. Verkerk, S. Schärpe, M. Maes, Neuroendocrinology Lett. 2007, 28, 449-455;
12. l) F. P. Zemlan, W. O. Patent Appl. 2006105455, 2006;
13. Chem. Abstr. 2006, 145: 370216, 1041366.
14. For a review on the Friedel-Crafts reactions see: a) G. A. Olah, R. Krishnamurti, G. K. S. Prakash, Friedel-Crafts Alkylations, in: Comprehensive Organic Synthesis, Vol.3, (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, pp 293-339.
15. For reviews, on enantioselective Friedel-Crafts reactions see: b) M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560-566;
16. Angew. Chem. Int. Ed. 2004, 43, 550-556;
17. c) K. A. Jørgensen, Synthesis 2003, 1117-1125;
18. d) M. Bandini, A. Melloni, S. Tommasi, A. UmaniRonchi, Synlett 2005, 1199-1222;
19. e) T. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108, 2903-2915.
20. K. B. Jensen, J. Thorhauge, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 2001, 113, 164-167;
21. Angew. Chem. Int. Ed. 2001, 40, 160-163.
22. a) D. A. Evans, K. A. Scheidt, K. R. Frandrick, H. W. Wu, J. Lam, J. Am. Chem. Soc. 2003, 125, 10780-10781;
23. b) H. Yang, Y.-T. Hong, S. Kim, Org. Lett. 2007, 9, 2281-2284.
24. a) W. Zhuang, T. Hausen, K. A. Jørgensen, Chem. Commun. 2001, 347-348;
25. b) J. Zhou, Y. Tang, J. Am. Chem. Soc. 2002, 124, 9030-9031;
26. c) J. Zhou, Y. Tang, Chem. Commun. 2004, 432-433;
27. d) J. Zhou, M.-C. Ye, Z.-Z. Huang, Y. Tang, J. Org. Chem. 2004, 69, 1309-1320.
28. C. Palomo, M. Oiarbide, B. G. Kardak, J. M. Garcia, A. Linden, J. Am. Chem. Soc. 2005, 127, 4154-4155.
29. a) D. A. Evans, K. R. Fandrick, H.J. Song, J. Am. Chem. Soc. 2005, 127, 8942-8943;
30. b) N. Takenaka, J. P. Abell, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 742-743.
31. M. Bandini, A. Melloni, S. Tommasi, A. UmaniRonchi, Helv. Chim. Acta 2003, 86, 3753-3763.
32. P. K. Singh, V. K. Singh, Org. Lett. 2008, 10, 4121-4124.
33. C. Cao, Y. Zhou, X. Sun, Y. Tang, Tetrahedron 2008, 64, 10676-10680.
34. M. P. Sibi, J. Coulomb, L. M. Stanley, Angew. Chem. 2008, 120, 10061-10063;
35. Angew. Chem. Int. Ed. 2008, 47, 9913-9915.
36. A. J. Boersma, B. L. Feringa, G. Roelfes, Angew. Chem. Int. Ed. 2009, 48, 3346-3348.
37. Y. Liu, D. Shang, X. Zhou, X. Liu, X. Feng, Chem. Eur. 7 2009, 25, 2055-2058.
38. a) W. Zhuang, R. G. Hazell, K. A. Jørgensen, Org. Biomol. Chem. 2005, 3, 2566-2571;
39. b) R. P. Herrera, V. Sgarzani, L. Bernardi, A. Ricci, Angew. Chem. 2005, 117, 6734-6737;
40. Angew. Chem. Int. Ed. 2005, 44, 6576-6579;
41. c) Y. X. Jia, S. F. Zhu, Y. Yang, Q. L. Zhou, J. Org. Chem. 2006, 71, 75-80;
42. d) J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2008, 120, 4080-4082;
43. Angew. Chem. Int. Ed. 2008, 47, 4016-4018.
44. a) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370-4371;
45. b) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172-1173;
46. c) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894-7895;
47. d) L. Hong, L. Wang, C. Chen, B. Zhang, R. Wang Adv. Synth. Catal. 2009, 351, 772-778.
48. a) M. Bandini, M. Fagioli, M. Garavelli, A. Melloni, V. Irigari, A. Umani-Ronchi, J. Org. Chem. 2004, 69, 7511-7518;
49. b) M. Bandini, M. Fagioli, P. Melchiorre, A. Melloni, A. Umani-Ronchi, Tetrahedron Lett. 2003, 44, 5843-5846;
50. c) M. Terada, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 292-293;
51. d) G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403-1405;
52. e) W. Chen, W. Du. , L. Yue, R. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Org. Biomol. Chem. 2007, 5, 816-821.
53. Z. Jiang, Y. Yang, Y. Pan, Y. Zhao, H. Liu, C.-H. Tan, Chem. Eur. J. 2009, 15, 4925-4930.
54. D. Seebach, Angew. Chem. 1979, 91, 259-278;
55. Angew. Chem. Int. Ed. Engl. 1979, 18, 239-258.
56. J. L. Zigterman, J. C. S. Woo, S. D. Walker, J. S. Tedrow, C. J. Borths, E. E. Bunel, M. M. Faul, J. Org. Chem. 2007, 72, 8870-8876.
57. a) R. Kino, K. Daikai, T. Kawanami, H. Furuno, J. Inanaga, Org. Biomol. Chem. 2004, 2, 1822-1824;
58. b) H. S. P. Rao, S. P. Senthikumar, J. Org. Chem. 2004, 69, 2591-2594;
59. c) T. Geller, C. M. Krüger, H. C. Militzer, Tetrahedron Lett. 2004, 45, 5069-5071.
60. G. Blay, I. Fernández, J. R. Pedro, C. Vila, Org. Lett. 2007, 9, 2601-2604.
61. For reviews on asymmetric catalysis using BINOL: a) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187-2210;
62. b) J. M. Brunei, Chem. Rev. 2005, 105, 857-898;
63. c) M. Shibasaki, S. Matsunaga, Chem. Soc. Rev. 2006, 35, 269-279.
64. For some examples of asymmetric catalysis with Ti(IV) complexes see : a) R. Yu, Y. Yamashita, S. Kobayashi, Adv. Synth. Catal. 2009, 351, 147-152;
65. b) B. Zeng, X. Zhou, X. Liu, X. Feng, Tetrahedron 2007, 63, 5129-5136;
66. c) H. Bao, J. Zhou, Z. Wang, Y. Guo, T. You, K. Ding, J. Am. Chem. Soc. 2008, 130, 10116-10127;
67. d) Y. N. Belokon, J. Hunt, M. North, Tetrahedron: Asymmetry 2008, 19, 2804-2815;
68. e) T. Hashimoto, M. Omote, K. Maruoka, Org. Biomol. Chem. 2008, 6, 2263-2265.
69. For some examples of asymmetric catalysis with Hf(IV) complexes see: f) H. Hanawa, S. Kii, N. Asao, K. Maruoka, Tetrahedron Lett. 2000, 41, 5543-5546;
70. g) S. Kobayashi, S. Ogawa, C. Ogawa, M. Kawamura, M. Sugiura, Synlett 2001, 983-985;
71. h) D. A. Watson, M. Chiu, R. G. Bergman, Organometallics 2006, 25, 4731-4733;
72. i) S. Kobayashi, R. Yazaki, K. Seki, M. Ueno, Tetrahedron 2007, 63, 8425-8429.
73. Y. Yamashita, H. Ishitani, H. Shimizu, S. Kobayashi, J. Am. Chem. Soc. 2002, 124, 3292-3302.
74. C. Vila, Grad. Dissertation, Universität de Valencia, Burjassot, Spain 2007.
75. C. Vila, CCDC 732229 contains the supplementary crystallography 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.
76. T. Satyanarayana, S. Abraham, H. B. Kagan, Angew. Chem. 2009, 121, 464-503;
77. Angew. Chem. Int. Ed. 2009, 48, 456-494.
78. Octahedrical T. S. have been proposed for reactions catalyzed with Zr-BINOL complexes : a) H. Ishitani, M. Ueno, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 8180-8186;
79. b) Y. Ihori, Y. Yamashita, H. Ishitani, S. Kobayashi, J. Am. Chem. Soc. 2005, 127, 15528-15535.
80. a) R. E. Lutz, Organic Syntheses, Coll. Vol.3, 1955, pp 248-249;
81. b) S. Mataka, K. Takahasi, M. Tashiro, W. H. Lin, S. Iwasaki, T. Tsutsi, S. Saito, S. Akiyama, T. Yonemitsu, J. Heterocycl. Chem. 1989, 26, 215-219;
82. c) H. S. P. Rao, S. P. Senthilkumar, K. Jeyalakshmi, Heterocycl. Commun. 2003, 9, 65-71;
83. d) J.-T. Huang, T.-L. Su, K. A. Watanabe, J. Org. Chem. 1991, 56, 4811-4815;
84. e) E. Campaigne, W. O. Foye, J. Org. Chem. 1952, 27, 1405-1412.