Samarium diiodide induced cyclizations of γ-,δ-and ε-indolyl ketones: Reductive coupling, intermolecular trapping, and subsequent transformations of indolines

Chemistry - A European Journal

Volumn 17, Issue 35, 2011, Pages 9720-9730

  Beemelmanns, Christine ^a   Lentz, Dieter ^a   Reissig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

cyclization; indoles; ketyl coupling; radical reactions; samarium

Indexed keywords

ACID CHLORIDES; AFTER-TREATMENT; ALKANONES; CHEMICAL TRANSFORMATIONS; COMPREHENSIVE STUDIES; CYCLIZATION PRODUCTS; CYCLIZATIONS; DIASTEREOMERS; ELECTROPHILES; GOOD YIELD; INDOLE ALKALOIDS; INDOLE DERIVATIVES; INDOLES; INDOLINE DERIVATIVES; INTERMOLECULAR TRAPPING; KETYL COUPLING; METATHESIS REACTIONS; N-ALKYLATION; QUATERNARY CENTERS; RADICAL REACTIONS; REDUCTIVE COUPLINGS; SAMARIUM DIIODIDE; STRUCTURAL MOTIFS; SYNTHETIC BUILDING BLOCKS;

CHLORINE COMPOUNDS; KETONES; ORGANIC COMPOUNDS; REACTION KINETICS; SAMARIUM;

CYCLIZATION;

EID: 80051778750     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100981     Document Type: Article

References (141)

1. G. J. Rowlands, Tetrahedron 2009, 65, 8603-8655
2. G. J. Rowlands, Tetrahedron 2010, 66, 1593-1636.
3. For selected reviews, see
4. P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206
5. W. Zhang, Curr. Org. Chem. 2004, 8, 757-780
6. G. S. C. Srikanth, S. L. Castle, Tetrahedron 2005, 61, 10377-10441.
7. J.-L. Namy, H. B. Kagan, Nouv. J. Chim. 1977, 1, 5-7
8. P. Girard, J.-L. Namy, H. B. Kagan, J. Am. Chem. Soc. 1980, 102, 2693-2698.
9. For selected reviews on samarium diiodide promoted reactions
10. F. A. Khan, R. Zimmer, J. Prakt. Chem. 1997, 339, 101-104
11. A. Krief, A.-M. Laval, Chem. Rev. 1999, 99, 745-777
12. H. B. Kagan, Tetrahedron 2003, 59, 10351-10372
13. M. Berndt, S. Gross, A. Hölemann, H.-U. Reissig, Synlett 2004, 422-438
14. K. Gopalaiah, H. Kagan, New J. Chem. 2008, 32, 607-637
15. I. M. Rudkin, L. C. Miller, D. J. Procter, Organomet. Chem. 2008, 34, 19-45
16. D. J. Procter, R. A. Flowers II, T. Skrydstrup, Organic Synthesis Using Samarium Diioide, RSC, Cambridge, 2009
17. C. Beemelmanns, H.-U. Reissig, Chem. Soc. Rev. 2011, 40, 2199-2210.
18. G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307-338
19. G. A. Molander, C. R. Harris, Tetrahedron 1998, 54, 3321-3354.
20. F. A. Khan, R. Czerwonka, R. Zimmer, H.-U. Reissig, Synlett 1997, 995-997
21. E. Nandanan, C. U. Dinesh, H.-U. Reissig, Tetrahedron 2000, 56, 4267-4277
22. A. Hölemann, H.-U. Reissig, Synlett 2004, 2732-2735
23. H.-U. Reissig, F. A. Khan, R. Czerwonka, C. U. Dinesh, A. L. Shaikh, R. Zimmer, Eur. J. Org. Chem. 2006, 4419-4428
24. J. Saadi, D. Lentz, H.-U. Reissig, Org. Lett. 2009, 11, 3334-3337
25. J. Saadi, H.-U. Reissig, Synlett 2009, 2089-2092
26. J. Saadi, I. Brüdgam, H.-U. Reissig, Beilstein J. Org. Chem. 2010, 6, 1229-1245.
27. 2-induced ketyl-alkene couplings, see
28. K. Otsubo, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 5763-5764
29. S. Fukuzawa, A. Nakanishi, T. Fujinami, S. Sakai, J. Chem. Soc. Perkin Trans. 1 1988, 1669-1675
30. E. J. Enholm, A. Trivellas, Tetrahedron Lett. 1989, 30, 1063-1066
31. E. J. Enholm, H. Satici, A. Trivellas, J. Org. Chem. 1989, 54, 5841-5843
32. D. J. Johnston, E. Couché, D. J. Edmonds, K. W. Muir, D. J. Procter, Org. Biomol. Chem. 2003, 1, 328-337.
33. 2-induced reactions in natural product synthesis, see
34. D. J. Edmonds, D. Johnston, D. J. Procter, Chem. Rev. 2004, 104, 3371-3404
35. K. C. Nicolaou, S. P. Ellery, J. S. Chen, Angew. Chem. 2009, 121, 7276-7301
36. Angew. Chem. Int. Ed. 2009, 48, 7140-7165.
37. C. U. Dinesh, H.-U. Reissig, Angew. Chem. 1999, 111, 874-876
38. Angew. Chem. Int. Ed. 1999, 38, 789-791.
39. 2 arene-carbonyl couplings, see
40. H.-G. Schmalz, S. Siegel, J. W. Bats, Angew. Chem. 1995, 107, 2597-2599
41. Angew. Chem. Int. Ed. Engl. 1995, 34, 2383-2385
42. J.-S. Shiue, M.-H. Lin, J.-M. Fang, J. Org. Chem. 1997, 62, 4643-4649
43. C.-W. Kuo, J.-M. Fang, Synth. Commun. 2001, 31, 877-892
44. H. Ohno, S. Maeda, M. Okumura, R. Wakayama, T. Tanaka, Chem. Commun. 2002, 316-317
45. H. Ohno, R. Wakayama, S. Maeda, H. Iwasaki, M. Okumura, C. Iwata, H. Mikamiyama, T. Tanaka, J. Org. Chem. 2003, 68, 5909-5916
46. H. Ohno, M. Okumura, S. Maeda, H. Iwasaki, R. Wakayama, T. Tanaka, J. Org. Chem. 2003, 68, 7722-7732.
47. Reviews dealing with synthetic applications of dearomatizing processes: for reductive dearomatizations, see
48. L. N. Mander, Synlett 1991, 134-144
49. T. J. Donohoe, R. Garg, C. A. Stevenson, Tetrahedron: Asymmetry 1996, 7, 317-344
50. A. G. Schultz, Chem. Commun. 1999, 1263-1271; for nucleophilic dearomatizations, see
51. J. Clayden, M. N. Kenworthy, Synthesis 2004, 1721-1736
52. F. López Ortiz, M. J. Iglesias, I. Fernández, C. M. A. Sánchez, G. R. Gómez, Chem. Rev. 2007, 107, 1580-1691
53. G. Barbe, G. Pelletier, A. B. Charette, Org. Lett. 2009, 11, 3398-3401; for transition-metal-mediated dearomatizations, see
54. T. Bach, Angew. Chem. 1996, 108, 795-796
55. Angew. Chem. Int. Ed. Engl. 1996, 35, 729-730
56. A. R. Pape, K. P. Kaliappan, E. P. Kündig, Chem. Rev. 2000, 100, 2917-2940; for oxidative dearomatizations, see
57. S. Quideau, L. Pouységu, D. Deffieux, Synlett 2008, 467-495, and references therein; for a recent general review, see
58. S. P. Roche, J. A. Porco, Jr., Angew. Chem. 2011, 123, 4154-4170
59. Angew. Chem. Int. Ed. 2011, 50, 4068-4093.
60. For the intramolecular additions of samarium ketyl to aryl groups, see
61. M. Berndt, I. Hlobilová, H.-U. Reissig, Org. Lett. 2004, 6, 957-960
62. U. K. Wefelscheid, M. Berndt, H.-U. Reissig, Eur. J. Org. Chem. 2008, 3635-3646
63. U. K. Wefelscheid, H.-U. Reissig, Adv. Synth. Catal. 2008, 350, 65-69
64. U. K. Wefelscheid, H.-U. Reissig, Tetrahedron: Asymmetry 2010, 21, 1601-1610
65. A. Niermann, H.-U. Reissig, Synlett 2011, 525-528.
66. F. Aulenta, M. Berndt, I. Brüdgam, H. Hartl, S. Sörgel, H.-U. Reissig, Chem. Eur. J. 2007, 13, 6047-6062.
67. S. Gross, H.-U. Reissig, Org. Lett. 2003, 5, 4305-4307
68. V. Blot, H.-U. Reissig, Eur. J. Org. Chem. 2006, 4989-4992
69. V. Blot, H.-U. Reissig, Synlett 2006, 2763-2766
70. C. Beemelmanns, H.-U. Reissig, Org. Biomol. Chem. 2009, 7, 4475-4480
71. C. Beemelmanns, V. Blot, S. Gross, D. Lentz, H.-U. Reissig, Eur. J. Org. Chem. 2010, 2716-2732
72. C. Beemelmanns, H.-U. Reissig, Angew. Chem. 2010, 122, 8195-8199
73. Angew. Chem. Int. Ed. 2010, 49, 8021-8025.
74. For selected reviews on indole synthesis and indole-containing natural products, see
75. R. J. Sundberg, in The Chemistry of Indoles, Academic Press, New York, 1970
76. R. J. Sundberg, in Indoles, Academic Press, London, 1996
77. J. Bonjoch, J. Bosch, in The Alkaloids, Vol. 48 (Ed.:, G. A. Cordell,), Academic Press, San Diego, 1996, pp. 75-189
78. G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045-1075
79. J. Bonjoch, D. Solé, Chem. Rev. 2000, 100, 3455-3482
80. M. Somei, F. Yamada, Nat. Prod. Rep. 2005, 22, 73-103
81. G. R. Humphrey, T. Kuethe, Chem. Rev. 2006, 106, 2875-2911
82. K. Higuchi, T. Kawasaki, Nat. Prod. Rep. 2007, 24, 843-868; for selected reviews dealing with indolizidines, see
83. A. S. Howard, J. P. Michael, in The Alkaloids, Vol. 28 (Ed.:, A. Brossi,), Academic Press, New York, 1986, pp. 183-308
84. A. D. Elbein, R. J. Molyneux, in Alkaloids: Chemical and Biological Perspectives, Vol. 5 (Ed.:, S. W. Pelletier,), Wiley, New York, 1987, pp. 1-54
85. R. Ben-Othman, M. Othman, K. Ciamala, M. Knorr, C. Strohmann, B. Decroix, Tetrahedron 2009, 65, 4846-4854; for selected reviews on pyrrolizidine derivatives, see
86. C. Christophersen, in The Alkaloids, Vol. 24 (Ed.:, A. Brossi,), Academic Press, Orlando, 1985, pp. 25-98
87. D. J. Robins, Nat. Prod. Rep. 1995, 12, 413-418
88. J. R. Liddell, Nat. Prod. Rep. 2000, 17, 455-462
89. S. Agarwal, S. Cämmerer, S. Filali, W. Fröhner, J. Knöll, M. P. Krahl, K. R. Reddy, H.-J. Knölker, Curr. Org. Chem. 2005, 9, 1601-1614
90. A. Brandi, F. Cardona, S. Cicchi, F. M. Cordero, A. Goti, Chem. Eur. J. 2009, 15, 7808-7821, and references therein.
91. For selected reviews on strychnos alkaloids, see
92. R. Huisgen, Angew. Chem. 1950, 62, 527-534
93. see reference [15f]
94. J. Buckingham, Bitter Nemesis-The Intimate History of Strychnine, CRC Press, New York, 2008
95. K. C. Nicolaou, T. Montagnon, Molecules that Changed the World, Wiley-VCH, Weinheim, 2008, pp. 91-96
96. M. Mori, Heterocycles 2010, 81, 259-292.
97. For related processes of situ trapping of samarium enolates, see, for example
98. G. A. Molander, J. A. McKie, J. Org. Chem. 1992, 57, 3132-3139
99. E. J. Enholm, A. Trivellas, Tetrahedron Lett. 1994, 35, 1627-1628
100. M. D. Helm, M. Da Silva, D. Sucunza, T. J. K. Findley, D. J. Procter, Angew. Chem. 2009, 121, 9479-9481
101. Angew. Chem. Int. Ed. 2009, 48, 9315-9317
102. M. D. Helm, M. Da Silva, D. Sucunza, M. Helliwell, D. J. Procter, Tetrahedron 2009, 65, 10816-10829.
103. For the preparation of starting materials see the Supporting Information.
104. N. Kise, T. Mano, T. Sakurai, Org. Lett. 2008, 10, 4617-4620.
105. A. L. J. Beckwith, Tetrahedron 1981, 37, 3073-3100
106. D. C. Spellmeyer, K. N. Houk, J. Org. Chem. 1987, 52, 959-974.
107. J. Inanaga, M. Ishikawa, M. Yamaguchi, Chem. Lett. 1987, 1485-1486
108. Z. Hou, Y. Wakatsuki, J. Chem. Soc. Chem. Commun. 1994, 1205-1206
109. E. Prasad, R. A. Flowers II, J. Am. Chem. Soc. 2002, 124, 6895-6899
110. A. Dahlén, G. Hilmersson, Eur. J. Inorg. Chem. 2004, 3393-3403
111. T. Inokuchi, J. Org. Chem. 2005, 70, 1497-1500
112. R. A. Flowers II, Synlett 2008, 1427-1439
113. D. V. Sadasivam, P. K. S. Antharjanam, E. Prasad, R. A. Flowers II, J. Am. Chem. Soc. 2008, 130, 7228-7229
114. H. Farran, S. Hoz, J. Org. Chem. 2009, 74, 2075-2079
115. C. E. McDonald, J. D. Ramsey, D. G. Sampsell, J. A. Butler, M. R. Cecchini, Org. Lett. 2010, 12, 5178-5181.
116. ORTEP-3 for windows:, L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
117. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
118. Selected recent reviews dealing with cross-metathesis
119. R. H. Grubbs, in Handbook of Metathesis, Wiley-VCH, Weinheim, 2003
120. S. J. Connon, S. Blechert, Angew. Chem. 2003, 115, 1944-1968
121. Angew. Chem. Int. Ed. 2003, 42, 1900-1923
122. S. Monfette, D. E. Fogg, Chem. Rev. 2009, 109, 3783-3816.
123. Selected recent reviews dealing with spirocyclic indole derivatives
124. C. Marti, E. M. Carreira, Eur. J. Org. Chem. 2003, 2209-2219
125. C. V. Galliford, K. A. Scheidt, Angew. Chem. 2007, 119, 8902-8912
126. Angew. Chem. Int. Ed. 2007, 46, 8748-8758.
127. K. I. Booker-Milburn, M. Fedouloff, S. Paknoham, J. B. Strachan, J. L. Melville, M. Voyle, Tetrahedron Lett. 2000, 41, 4657-4661
128. J. C. Hodges, W. Wang, F. Riley, J. Org. Chem. 2004, 69, 2504-2508
129. M. Rottmann, C. McNamara, B. K. S. Yeung, M. C. S. Lee, B. Zou, B. Russell, P. Seitz, D. M. Plouffe, N. V. Dharia, J. Tan, S. B. Cohen, K. R. Spencer, G. E. González-Páez, S. B. Lakshminarayana, A. Goh, R. Suwanarusk, T. Jegla, E. K. Schmitt, H.-P. Beck, R. Brun, F. Nosten, L. Renia, V. Dartois, T. H. Keller, D. A. Fidock, E. A. Winzeler, T. T. Diagana, Science 2010, 329, 1175-1180.
130. Selected reviews on [3+2]-cycloadditions, see
131. R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry (Ed.:, A. Padwa,), Wiley, New York, 1984, pp. 1-176
132. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075
133. Angew. Chem. Int. Ed. 2001, 40, 2004-2021
134. J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249-1262.
135. T. R. Chan, R. Hilgraf, K. B. Sharpless, V. V. Fokin, Org. Lett. 2004, 6, 2853-2855
136. A. Al-Harrasi, F. Pfrengle, V. Prisyazhnyuk, S. Yekta, P. Koos, H.-U. Reissig, Chem. Eur. J. 2009, 15, 11632-11641.
137. L. F. Tietze, H. P. Bell, S. Chandrasekhar, Angew. Chem. 2003, 115, 4128-4160
138. Angew. Chem. Int. Ed. 2003, 42, 3996-4028
139. G. Mehta, V. Singh, Chem. Soc. Rev. 2002, 31, 324-334
140. K. Suzuki, Chem. Rec. 2010, 10, 291-307.
141. SHELX97, Programs for Crystal Structure Analysis, Release 97-2, G. M. Sheldrick, University of Göttingen (Germany), 1998.