Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: Reaction development and applications

Chemistry - A European Journal

Volumn 17, Issue 10, 2011, Pages 2916-2922

  Trost, Barry M ^a   Zhang, Yong ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

alkylation; asymmetric catalysis; molybdenum; natural products; total synthesis

Indexed keywords

ASYMMETRIC ALLYLIC ALKYLATION REACTIONS; ASYMMETRIC ALLYLIC ALKYLATIONS; ASYMMETRIC CATALYSIS; CATALYZED REACTIONS; INDOLINE ALKALOIDS; NATURAL PRODUCTS; TOTAL SYNTHESIS;

ALKYLATION; CATALYSIS; ENANTIOSELECTIVITY; MOLYBDENUM; NUCLEOPHILES;

SYNTHESIS (CHEMICAL);

ALKALOID; COMMUNESIN B; DEBROMOFLUSTRAMINE B; DRUG DERIVATIVE; FUSED HETEROCYCLIC RINGS; HALOGENATED HYDROCARBON; INDOLE DERIVATIVE; MOLYBDENUM; OXINDOLE; PEROPHORAMIDINE; PHENSERINE; PHYSOSTIGMINE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; ALKYLATION; CATALYSIS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HYDROCARBONS, HALOGENATED; INDOLES; MOLECULAR STRUCTURE; MOLYBDENUM; PHYSOSTIGMINE; STEREOISOMERISM;

EID: 79951982503     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002569     Document Type: Article

References (88)

1. For recent reviews of oxindole alkaloids, see
2. C. Marti, E. M. Carreira, Eur. J. Org. Chem. 2003, 2209
3. C. V. Galliford, K. A. Scheit, Angew. Chem. 2007, 119, 8902
4. Angew. Chem. Int. Ed. 2007, 46, 8748
5. B. M. Trost, M. K. Brennan, Synthesis 2009, 3003.
6. For recent synthesis of oxindole alkaloids, see
7. P. S. Baran, J. M. Richter, J. Am. Chem. Soc. 2005, 127, 15394
8. B. M. Trost, N. Cramer, H. Bernsmann, J. Am. Chem. Soc. 2007, 129, 3086
9. G. D. Artman, A. W. Grubbs, R. M. Williams, J. Am. Chem. Soc. 2007, 129, 6336.
10. P. L. Julian, J. Pikl, J. Am. Chem. Soc. 1935, 57, 755
11. A. D. Lebsack, J. T. Link, L. E. Overman, B. A. Steans, J. Am. Chem. Soc. 2002, 124, 9008.
12. For recent reviews, see
13. C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363
14. B. M. Trost, C. Jiang, Synthesis 2006, 369.
15. T. B. K. Lee, G. S. K. Wong, J. Org. Chem. 1991, 56, 872.
16. Heck Reaction
17. T. Matsuura, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6500
18. A. Ashimori, B. Bachand, M. A. Calter, S. P. Govek, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6488
19. A. Ashimori, B. Bachand, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6477.
20. Rearrangement of O-acyl or O-alkyloxindoles
21. I. D. Hills, G. C. Fu, Angew. Chem. 2003, 115, 4051
22. Angew. Chem. Int. Ed. 2003, 42, 3921
23. T. A. Duffey, S. A. Shaw, E. Vedejs, J. Am. Chem. Soc. 2009, 131, 14
24. E. C. Linton, M. C. Kozlowski, J. Am. Chem. Soc. 2008, 130, 16162.
25. Cross-coupling of prochiral enolate
26. S. Lee, J. F. Hartwig, J. Org. Chem. 2001, 66, 3402
27. E. P. Kündig, T. M. Seidel, Y. Jia, G. Bernardinelli, Angew. Chem. 2007, 119, 8636
28. Angew. Chem. Int. Ed. 2007, 46, 8484
29. A. M. Taylor, R. A. Altman, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 9900.
30. Michael Addition
31. R. He, C. Ding, K. Maruoka, Angew. Chem. 2009, 121, 4629
32. Angew. Chem. Int. Ed. 2009, 48, 4559
33. T. Bui, S. Syed, C. F. Barbas III, J. Am. Chem. Soc. 2009, 131, 8758
34. Y. Kato, M. Furutachi, Z. Chen, H. Mitsunuma, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 9168.
35. Cycloaddition
36. B. M. Trost, N. N. Cramer, S. M. Silverman, J. Am. Chem. Soc. 2007, 129, 12396
37. G. Bencivenni, L. Y. Wu., A. Mazzanti, B. Giannichi, F. Pesciaioli, M. P. Song, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7336
38. X. H. Chen, Q. Wei, S. W. Luo, H. Xiao, L. Z. Gong, J. Am. Chem. Soc. 2009, 131, 13819.
39. Allylic Alkylation
40. B. M. Trost, M. U. Frederiksen, Angew. Chem. 2005, 117, 312
41. Angew. Chem. Int. Ed. 2005, 44, 308
42. B. M. Trost, Y. Zhang, J. Am. Chem. Soc. 2006, 128, 4590
43. B. M. Trost, Y. Zhang, J. Am. Chem. Soc. 2007, 129, 14548
44. B. M. Trost, Y. Zhang, Chem. Eur. J. 2010, 16, 296.
45. Other transformations
46. Y. Yasui, H. Kamisaki, Y. Takemoto, Org. Lett. 2008, 10, 3303
47. S. Ma, X. Han, S. Krishnan, S. C. Virgil, B. M. Stoltz, Angew. Chem. 2009, 121, 8181
48. Angew. Chem. Int. Ed. 2009, 48, 8037
49. Y. Nakao, S. Ebata, A. Yada, T. Hiyama, M. Ikawa, S. Ogoshi, J. Am. Chem. Soc. 2008, 130, 12874.
50. For recent reviews, see
51. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921
52. B. M. Trost, T. Zhang, J. D. Sieber, Chem. Sci. 2010, 1, 427.
53. B. M. Trost, J. Xu, J. Am. Chem. Soc. 2005, 127, 17180
54. B. M. Trost, J. Xu, T. Schmidt, J. Am. Chem. Soc. 2008, 130, 11852.
55. D. C. Behenna, B. M. Stoltz, J. Am. Chem. Soc. 2004, 126, 15044
56. J. A. Enquist, Jr., B. M. Stoltz, Nature 2008, 453, 1228.
57. B. M. Trost, I. Hachiya, J. Am. Chem. Soc. 1998, 120, 1104.
58. M. Palucki, J. M. Um, N. Yasuda, D. A. Conlon, F. R. Tsay, F. W. Hartner, Y. Hsiao, B. Marcue, S. Karady, D. L. Hughes, P. G. Dormer, P. J. Reider, J. Org. Chem. 2002, 67, 5508.
59. S. W. Krska, D. L. Hughes, R. A. Reamer, D. J. Mathre, Y. Sun, B. M. Trost, J. Am. Chem. Soc. 2002, 124, 12656
60. S. W. Krska, D. L. Hughes, R. A. Reamer, D. J. Mathre, M. Palucki, N. Yasuda, Y. Sun, B. M. Trost, Pure Appl. Chem. 2004, 76, 625.
61. B. M. Trost, K. Dogra, J. Am. Chem. Soc. 2002, 124, 14320
62. B. M. Trost, K. Dogra, M. Franzini, J. Am. Chem. Soc. 2004, 126, 1944.
63. K. Szabó-Pusztay, L. Szabo, Synthesis 1979, 276.
64. N. Nakazawa, K. Tagami, H. Iimori, S. Sano, T. Ishikawa, Y. Nagao, S.-M. Tokushima, Heterocycles 2001, 55, 2157.
65. J. Jobst, O. Hesse, Justus Liebigs Ann. Chem. 1864, 129, 115.
66. N. H. Greig, X. F. Pei, T. T. Soncrant, D. K. Ingram, A. Brossi, Med. Res. Rev. 1995, 15, 3.
67. N. Sano, K. Bell, K. Marder, L. Stricks, Y. Stem. R. Mayeux, Clin. Neuropharmacol. 1993, 16, 61.
68. L. A. Sorbera, J. Castaner, Drugs Future 2003, 28, 18.
69. Q. S. Yu, H. W. Holloway, J. L. Flippen-Anderson, B. Hoffman, A. Brossi, N. H. Greig, J. Med. Chem. 2001, 44, 4062.
70. A. Brossi, X. F. Pei, N. H. Greig, Aust. J. Chem. 1996, 49, 171.
71. A. Huang, J. Kodanko, L. E. Overman, J. Am. Chem. Soc. 2004, 126, 14043.
72. R. Underwood, K. Prasad, O. Repic, G. E. Hardtmann, Synth. Commun. 1992, 22, 343.
73. J. S. Carle, C. Christophersen, J. Am. Chem. Soc. 1979, 101, 4012.
74. J. S. Carle, C. Christophersen, J. Org. Chem. 1980, 45, 1586
75. J. S. Carle, C. Christophersen, J. Org. Chem. 1981, 46, 3440.
76. T. Kawasaki, R. Terashima, K. Sakaguchi, H. Sekiguchi, M. Sakamoto, Tetrahedron Lett. 1996, 37, 7525
77. J. R. Fuchs, R. L. Funk, Org. Lett. 2005, 7, 677
78. T. Kawasaki, M. Shinada, K. Daigo, M. Ohzono, A. Ogawa, Chem. Commun. 2006, 420.
79. J. F. Austin, S. G. Kim, C. J. Sinz, W. J. Xiao, D. W. C. MacMillan, Proc. Natl. Acad. Sci. USA 2004, 101, 5482.
80. A. K. Chatterjee, D. P. Sanders, R. H. Grubbs, Org. Lett. 2002, 4, 1939.
81. A. Numata, C. Takahashi, Y. Ito, T. Takada, K. Kawai, Y. Usami, E. Matsumura, M. Imachi, T. Ito, T. Hasegawa, Tetrahedron Lett. 1993, 34, 2355.
82. S. M. Verbitski, C. L. Mayne, R. A. Davis, G. P. Concepcio, C. M. Ireland, J. Org. Chem. 2002, 67, 7124.
83. Racemic synthesis of perophoramidine:, J. R. Fuchs, R. L. Funk, J. Am. Chem. Soc. 2004, 126, 5068.
84. Racemic synthesis of communesin:, F. J. Yang, H. Wu, L. Shen, Y. Qin, J. Am. Chem. Soc. 2007, 129, 13794.
85. B. Andersen, J. Smedsgaard, J. C. Frisvad, J. Agric. Food Chem. 2004, 52, 2421
86. R. Jadulco, R. A. Edrada, R. Ebel, A. Berg, K. Schaumann, B. Wary, K. Steube, P. Proksch, J. Nat. Prod. 2004, 67, 78.
87. The use of base-induced elimination for generating o-azaxylylene has been reported:, H. Steinhagen, E. J. Corey, Angew. Chem. 1999, 111, 2054
88. Angew. Chem. Int. Ed. 1999, 38, 1928.