Bicyclic cyclopentenones via the combination of an iridium-catalyzed allylic substitution with a diastereoselective intramolecular pauson-khand reaction

Advanced Synthesis and Catalysis

Volumn 353, Issue 2-3, 2011, Pages 349-370

  Farwick, Andreas ^a   Engelhart, Jens U ^a   Tverskoy, Olena ^a   Welter, Carolin ^a   Umlauf Née Stang, Quendolin A ^a   Rominger, Frank ^a   Kerr, William J ^b   Helmchen, Günter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

alkaloids; alkyne ligands; allylic substitution; asymmetric catalysis; iridium; Pauson Khand reaction

Indexed keywords

EID: 79951827490     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000706     Document Type: Article

References (153)

1. S. M. Roberts, M. G. Santoro, E. S. Sickle, J. Chem. Soc. Perkin Trans. 1 2002, 1735-1742
2. M. Iqbal, P. Evans, A. Lledõ, X. Verdaguer, M. Pericßs, A. Riera, C. Loeffler, A. K. Sinha, M. J. Mueller, ChemBioChem 2005, 6, 276-280
3. A. Rossi, P. Kapahi, G. Natoli, T. Takahashi, Y. Chen, M. Karin, M. G. Santoro, Nature 2000, 403, 103-108.
4. I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, J. Chem. Soc. (D) 1971, 36
5. First intramolecular version:, N. E. Schore, M. C. Croudace, J. Org. Chem. 1981, 46, 5436-5438; reviews
6. S. E. Gibson (née Thomas), A. Stevenazzi, Angew. Chem. 2003, 115, 1844-1854
7. Angew. Chem. Int. Ed. 2003, 42, 1800-1810
8. J. Blanco-Urgoiti, L. Añorbe, L. Pérez-Serrano, G. Domíngez, J. Pérez-Castells, Chem. Soc. Rev. 2004, 33, 32-42
9. T. Shibata, Adv. Synth. Catal. 2006, 348, 2328-2336
10. H.-W. Lee, F.-Y. Kwong, Eur. J. Org. Chem. 2010, 789-811
11. O. Geis, H.-G. Schmalz, Angew. Chem. 1998, 110, 955-958
12. Angew. Chem. Int. Ed. 1998, 37, 911-914
13. K. M. Brummond, J. L. Kent, Tetrahedron 2000, 56, 3263-3283
14. J. Fletcher, S. R. D. Christie, J. Chem. Soc. Perkin Trans. 1 2001, 1-13.
15. For representative examples, see
16. C. Exon, P. Magnus, J. Am. Chem. Soc. 1983, 105, 2477-2478
17. S.-E. Yoo, S. H. Lee, J. Org. Chem. 1994, 59, 6968-6972
18. T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1997, 119, 4353-4363
19. S.-J. Min, S. J. Danishefsky, Angew. Chem. 2007, 119, 2249-2252
20. Angew. Chem. Int. Ed. 2007, 46, 2199-2202
21. J. J. Caldwell, I. D. Cameron, S. D. R. Christie, A. M. Hay, C. Johnstone, W. J. Kerr, A. Murray, Synthesis 2005, 3293-3296
22. A. Farwick, G. Helmchen, Org. Lett. 2010, 12, 1108-1111
23. D. C. Billington, W. J. Kerr, P. L. Pauson, J. Organomet. Chem. 1987, 328, 223-227
24. C. Johnstone, W. J. Kerr, U. Lange, J. Chem. Soc. Chem. Commun. 1995, 457-458
25. J. G. Donkervoort, A. R. Gordon., C. Johnstone, W. J. Kerr, U. Lange, Tetrahedron 1996, 52, 7391-7420
26. W. J. Kerr, M. McLaughlin, A. J. Morrison, P. L. Pauson, Org. Lett. 2001, 3, 2945-2948
27. J. J. Crawford, W. J. Kerr, M. McLaughlin, A. J. Morrison, P. L. Pauson, G. J. Thurston, Tetrahedron 2006, 62, 11360-11370
28. A. Vázquez-Romero, L. Cárdenas, E. Blasi, X. Verdaguer, A. Riera, Org. Lett. 2009, 11, 3104-3107
29. A. Vázquez-Romero, J. Rodríguez, A. Lledõ, X. Verdaguer, A. Riera, Org. Lett. 2008, 10, 4509-4512.
30. X. Verdaguer, J. Vázquez, G. Fuster, V. Bernardes-Génisson, A. E. Greene, A. Moyano, M. A. Pericßs, A. Riera, J. Org. Chem. 1998, 63, 7037-7052
31. M. R. Rivero, J. C. adeaLaaRosa, J. C. Carretero, J. Am. Chem. Soc. 2003, 125, 14992-14993
32. J. Adrio, J. C. Carretero, J. Am. Chem. Soc. 1999, 121, 7411-7412
33. S. Fonquerna, A. Moyano, M. A. Pericßs, A. Riera, J. Am. Chem. Soc. 1997, 119, 10225-10226.
34. A. M. Hay, W. J. Kerr, G. G. Kirk, D. Middlemiss, Organometallics 1995, 14, 4986-4988
35. D. T. Rutherford, S. D. R. Christie, Tetrahedron Lett. 1998, 39, 9805-9808
36. Y. Gimbert, F. Robert, A. Durif, M.-T. Averbuch, N. Kann, A. E. Greene, J. Org. Chem. 1999, 64, 3492-3497
37. S. J. Sturla, S. L. Buchwald, J. Org. Chem. 1999, 64, 5547-5550
38. T. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852-9853
39. A. R. Kennedy, W. J. Kerr, D. M. Lindsay, J. S. Scott, S. P. Watson, J. Chem. Soc. Perkin Trans. 1 2000, 4366-4372
40. J. Solß, M. Revés, A. Riera, X. Verdaguer, Angew. Chem. 2007, 119, 5108-5111
41. Angew. Chem. Int. Ed. 2007, 46, 5020-5023
42. X. Verdaguer, A. Lledõ, C. Lõpez-Mosquera, M. A. Maestro, M. A. Pericßs, A. Riera, J. Org. Chem. 2004, 69, 8053-8061
43. X. Verdaguer, A. Moyano, M. A. Pericßs, A. Riera, M. A. Maestro, J. Mahía, J. Am. Chem. Soc. 2000, 122, 10242-10243.
44. W. J. Kerr, G. G. Kirk, D. Middlemiss, Synlett 1995, 1085-1086
45. W. J. Kerr, D. M. Lindsay, E. M. Rankin, J. S. Scott, S. P. Watson, Tetrahedron Lett. 2000, 41, 3229-3233
46. V. Derdau, S. Laschat, P. G. Jones, Heterocycles 1998, 48, 1445-1453.
47. A. Quattropani, G. Anderson, G. Bernadinelli, E. P. Kündig, J. Am. Chem. Soc. 1997, 119, 4773-4774
48. C. Mukai, J. S. Kim, H. Sonobe, M. Hanaoka, J. Org. Chem. 1999, 64, 6822-6832
49. N. M. Heron, J. A. Adams, A. H. Hoveyda, J. Am. Chem. Soc. 1997, 119, 6205-6206
50. J. Marco-Contelles, J. Ruiz, Tetrahedron Lett. 1998, 39, 6393-6394
51. R. B. Grossman, Tetrahedron 1999, 55, 919-934.
52. N. Jeong, S. D. Seo, J. Y. Shin, J. Am. Chem. Soc. 2000, 122, 10220-10221.
53. N. Jeong, S. Lee, B. K. Sung, Organometallics 1998, 17, 3642-3644
54. N. Jeong, B. K. Sung, Y. K. Choi, J. Am. Chem. Soc. 2000, 122, 6771-6772.
55. P. A. Evans, J. D. Nelson, J. Am. Chem. Soc. 1998, 120, 5581-5582
56. P. A. Evans, J. E. Robinson, J. D. Nelson, J. Am. Chem. Soc. 1999, 121, 6761-6762
57. P. A. Evans, D. K. Leahy, J. Am. Chem. Soc. 2000, 122, 5012-5013
58. P. A. Evans, L. J. Kennedy, J. Am. Chem. Soc. 2001, 123, 1234-1235.
59. P. A. Evans, J. E. Robinson, J. Am. Chem. Soc. 2001, 123, 4609-4610.
60. D. C. Billington, W. J. Kerr, P. L. Pauson, J. Organomet. Chem. 1988, 341, 181-185
61. D. C. Billington, W. J. Kerr, P. L. Pauson, C. F. Farnocchi, J. Organomet. Chem. 1988, 356, 213-219
62. W. J. Kerr, G. G. Kirk, D. Middlemiss, J. Organomet. Chem. 1996, 519, 93-101
63. C. M. Gordon, M. Kiszka, I. R. Dunkin, W. J. Kerr, J. S. Scott, J. Gebicki, J. Organomet. Chem. 1998, 554, 147-154
64. C. J. Clements, D. Dumoulin, D. R. Hamilton, M. Hudecek, W. J. Kerr, M. Kiefer, P. H. Moran, P. L. Pauson, J. Chem. Res. 1998, (S) 636-637; (M) 2658-2677
65. W. J. Kerr, M. McLaughlin, P. L. Pauson, S. M. Robertson, Chem. Commun. 1999, 2171-2172
66. W. J. Kerr, D. M. Lindsay, S. P. Watson, Chem. Commun. 1999, 2551-2552
67. D. R. Carbery, W. J. Kerr, D. M. Lindsay, J. S. Scott, S. P. Watson, Tetrahedron Lett. 2000, 41, 3235-3238
68. W. J. Kerr, D. M. Lindsay, M. McLaughlin, P. L. Pauson, Chem. Commun. 2000, 1467-1468
69. J. G. Ford, W. J. Kerr, G. G. Kirk, D. M. Lindsay, D. Middlemiss, Synlett 2000, 1415-1418
70. D. S. Brown, E. Campbell, W. J. Kerr, D. M. Lindsay, A. J. Morrison, K. G. Pike, S. P. Watson, Synlett 2000, 1573-1576
71. W. J. Kerr, M. McLaughlin, P. L. Pauson, S. M. Robertson, J. Organomet. Chem. 2001, 630, 104-117
72. W. J. Kerr, M. McLaughlin, P. L. Pauson, J. Organomet. Chem. 2001, 630, 118-124
73. A. R. Kennedy, W. J. Kerr, M. McLaughlin, P. L. Pauson, Acta Crystallogr. 2001, C57, 1316-1318
74. J. A. Brown, T. Janecki, W. J. Kerr, Synlett 2005, 2023-2026
75. J. L. KÄdzia, W. J. Kerr, A. R. McPherson, Synlett 2010, 649-653
76. A. R. Kennedy, W. J. Kerr L. C. Paterson, A. Sutherland, Acta Crystallogr. 2010, C66, o 473 -o 474.
77. M. Ernst, G. Helmchen, Angew. Chem. 2002, 114, 4231-4234
78. Angew. Chem. Int. Ed. 2002, 41, 4054-4056
79. M. Schelwies, P. Dübon, G. Helmchen, Angew. Chem. 2006, 118, 2526-2529
80. Angew. Chem. Int. Ed. 2006, 45, 2466-2469
81. T. Hübscher, G. Helmchen, Synlett 2006, 1323-1326
82. P. Elsner, P. Jetter, K. Brödner, G. Helmchen, Eur. J. Org. Chem. 2008, 2551-2563
83. S. Förster, G. Helmchen, Synlett 2008, 831-836.
84. Reviews
85. R. Takeuchi, Synlett 2002, 1954-1965
86. G. Helmchen, A. Dahnz, P. Dübon, M. Schelwies, R. Weihofen, Chem. Commun. 2007, 675-691
87. H. Miyabe, Y. Takemoto, Synlett 2005, 1641-1655
88. G. Helmchen, in: Iridium Complexes in Organic Synthesis, (Eds.:, A. Oro, C. Claver,), Wiley-VCH, Weinheim, Germany, 2009, ppa 211-250
89. G. Helmchen, U. Kazmaier, S. Förster, in: Catalytic Asymmetric Sythesis, (Ed.:, I. Ojima,), Wiley, Hoboken. 2010, ppa 497-641.
90. J.-B. Xia, W.-B. Liu, T.-M. Wang, S.-L. You, Chem. Eur. J. 2010, 16, 6442-6446
91. M. Schelwies, Diploma Thesis, Univ. Heidelberg, 2005.
92. R. Takeuchi, M. Kashio, Angew. Chem. 1997, 109, 268-270
93. Angew. Chem. Int. Ed. Engl. 1997, 36, 263-265
94. First enantioselective variant:, J. P. Janssen, G. Helmchen, Tetrahedron Lett. 1997, 38, 8025-8026.
95. Preparation of L1:, D. Polet, A. Alexakis, Org. Lett. 2005, 7, 1621-1624
96. Preparation of L2:, K. Tissot-Croset, D. Polet, A. Alexakis, Angew. Chem. 2004, 116, 2480-2482
97. Angew. Chem. Int. Ed. 2004, 43, 2426-2428.
98. [15a]
99. A. Leitner, C. Shu, J. F. Hartwig, Org. Lett. 2005, 7, 1093-1096.
100. R. Weihofen, O. Tverskoy, G. Helmchen, Angew. Chem. 2006, 118, 5673-5676
101. Angew. Chem. Int. Ed. 2006, 45, 5546-5549.
102. C. M. Huwe, S. Blechert, Tetrahedron Lett. 1994, 35, 9537-9540
103. K. T. Sylvester, P. J. Chirik, J. Am. Chem. Soc. 2009, 131, 8772-8774.
104. B. L. Pagenkopf, D. B. Belanger, D. J. R. O'Mahony, T. Livinghouse, Synthesis 2000, 1009-1019.
105. S. Spiess, C. Welter, G. Franck, J.-P. Taquet, G. Helmchen, Angew. Chem. 2008, 120, 7764-7767
106. Angew. Chem. Int. Ed. 2008, 47, 7652-7655.
107. C. Shu, A. Leitner, J.F. Hartwig, 2 004, 116, 4901-4904; Angew. Chem. 2004, 116, 4901-4904; Angew. Chem. Int. Ed. 2004, 43, 4797-4800.
108. C. Gnamm, G. Franck, N. Miller, T. Stork, K. Brödner, G. Helmchen, Synthesis 2008, 3331-3350.
109. S. J. Pastine, S. W. Youn, D. Sames, Org. Lett. 2003, 5, 1055-1058.
110. [20]
111. M. Gärtner, R. Weihofen, G. Helmchen, unpublished results.
112. F. A. Hicks, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 11688-11689
113. F. A. Hicks, N. M. Kablaoui, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 5881-5898
114. F. A. Hicks, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 7026-7033.
115. T. Shibata, S. Kadowaki, M. Hirase, K. Takagi, Synlett 2003, 573-575.
116. T. Morimoto, K. Fuji, K. Tsutsumi, K. Kakiuchi, J. Am. Chem. Soc. 2002, 124, 3806-3807
117. T. Shibata, N. Toshida, K. Takagi, Org. Lett. 2002, 4, 1619-1621
118. T. Shibata, N. Toshida, K. Takagi, J. Org. Chem. 2002, 67, 7446-7450
119. K. Fuji, T. Morimoto, K. Tsutsumi, K. Kakiuchi, Angew. Chem. 2003, 115, 2511-2513
120. Angew. Chem. Int. Ed. 2003, 42, 2409-2411.
121. Catalytic microwave-promoted PKR: C.M. Pearson, PhD Thesis, University of Strathclyde, 2006. See also
122. S. Fischer, U. Groth, M. Jung, A. Schneider, Synlett 2002, 2023-2026.
123. S. Shambayati, W. E. Crowe, S. L. Schreiber, Tetrahedron Lett. 1990, 31, 5289-5292
124. N. Jeong, Y. K. Chung, B. Y. Lee, S. H. Lee, S.-E. Yoo, Synlett 1991, 204-206
125. A. R. Gordon, C. Johnstone, W. J. Kerr, Synlett 1995, 1083-1084.
126. T. Sugihara, M. Yamada, M. Yamaguchi, M. Nishizawa, Synlett 1999, 771-773.
127. J. A. Brown, S. Irvine, W. J. Kerr, C. M. Pearson, Org. Biomol. Chem. 2005, 3, 2396-2398.
128. P. Magnus, C. Exon, P. Albaugh-Robertson, Tetrahedron 1985, 41, 5861-5869.
129. S.-E. Yoo, S. H. Lee, N. Jeong, I. Cho, Tetrahedron Lett. 1993, 34, 3435-3438.
130. The synthesis of (-)-α-kainic acid has received considerable attention, and more than 20 total syntheses and formal total syntheses have been reported. First asymmetric total synthesis
131. W. Oppolzer, K. Thirring, J. Am. Chem. Soc. 1982, 104, 4978-4979. Syntheses based on asymmetric catalysis
132. M. D. Bachi, A. Melman, J. Org. Chem. 1997, 62, 1896-1898
133. Q. Xia, B. Ganem, Org. Lett. 2001, 3, 485-487
134. B. M. Trost, M. T. Rudd, Org. Lett. 2003, 5, 1467-1470. Syntheses based on Pauson-Khand reactions
135. S.-E. Yoo, S. H. Lee, J. Org. Chem. 1994, 59, 6968-6972
136. S. Takano, I. Inomata, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1992, 169-170.
137. P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936-3938.
138. J. W. Burton, J. S. Clark, S. Derrer, T. C. Stork, J. G. Bendall, A. B. Holmes, J. Am. Chem. Soc. 1997, 119, 7483-7498.
139. J. Clayden, F. E. Knowles, I. R. Baldwin, J. Am. Chem. Soc. 2005, 127, 2412-2413.
140. H. Sakaguchi, H. Tokuyama, T. Fukuyama, Org. Lett. 2007, 9, 1635-1638.
141. G. Helmchen, V. Prelog, Helv. Chim. Acta 1972, 55, 2599-2611.
142. Review: S.V. Ley, J. Norman, W.P. Griffith, S.P. Marsden, Synthesis 1994, 639-666
143. W.P. Griffith, S.V. Ley, G.P. Whitcombe, A.D. White, J. Chem. Soc. Chem. Commun. 1987, 1625-1627.
144. F. N. Tebbe, G. W. Parshall, G. S. Reddy, J. Am. Chem. Soc. 1978, 100, 3611-3613
145. S. H. Pine, R. Zahler, D. A. Evans, R. H. Grubbs, J. Am. Chem. Soc. 1980, 102, 3270-3272.
146. S. Takano, T. Sugihara, S. Satoh, K. Ogasawara, J. Am. Chem. Soc. 1988, 110, 6467-6471.
147. Y. Nishibayashi, T. Chiba, K. Ohe, S. Uemura, J. Chem. Soc. Chem. Commun. 1995, 1243-1244.
148. B. P. Bonzic, P. Eilbracht, Org. Lett. 2008, 10, 3433-3436.
149. The analytical data were in agreement with those of, W. Oppolzer, B. Stammen, Tetrahedron 1997, 53, 3577-3586.
150. The enantiomer has been previously described in the literature on a different route:, B. Chao, D. C. Dittmer, Tetrahedron Lett. 2001, 42, 5789-5792.
151. The analytical data were in agreement with those of, D. Sureshkumar, S. Koutha, S. Chandrasekaran, Eur. J. Org. Chem. 2007, 4543-4551.
152. G.M. Sheldrick, Bruker Analytical X-ray-Division, Madison, Wisconsin 2008.
153. G. M. Sheldrick, Acta. Cryst. 2008, A64, 112-122.