Transition metal-mediated routes to cyclopentenones

Journal of Organometallic Chemistry

Volumn 689, Issue 24 SPEC. ISS., 2004, Pages 3873-3890

  Gibson, Susan E ^a   Lewis, Sara E ^a   Mainolfi, Nello ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Catalysis; Cyclopentenone; Natural products; Synthesis; Transition metals

Indexed keywords

SYNTHESIS (CHEMICAL); TRANSITION METALS;

CYCLOPENTENONES; ORGANIC SYNTHESIS;

AROMATIC COMPOUNDS;

CYCLOPENTENONE DERIVATIVE; TRANSITION ELEMENT;

CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; PHYSICAL CHEMISTRY; REVIEW;

EID: 9944247495     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2004.04.045     Document Type: Review

References (170)

1. H-W. Frühauf Chem. Rev. 97 1997 523
2. R.A. Ellison Synthesis 1973 397
3. B.M. Trost Angew. Chem. Int. Ed. 25 1986 1
4. R. Noyori, and M. Suzuki Angew. Chem. Int. Ed. 23 1984 847
5. R. Noyori, H. Koyano, M. Mori, R. Hirata, Y. Shiga, T. Kokura, and M. Suzuki Pure Appl. Chem. 66 1994 1999
6. S.M. Roberts, M. Gariella Santoro, and E.S. Sickle J. Chem. Soc., Perkin Trans. 1 2002 1735
7. D.S. Straus, and C.K. Glass Med. Res. Rev. 21 2001 185
8. A. Ross, P. Kapachi, G. Natoli, T. Takahashi, Y. Chen, and N. Karin Nature. 403 2000 103
9. T. Bui, and D.S. Straus Biochem. Biophys. Acta 31 1998 1397
10. T. Kato, M. Fukushima, S. Kurozumi, and R. Noyori Cancer Res. 46 1986 3538
11. M. Fukushima, T. Kato, S. Narumiya, Y. Mizushima, H. Sasaki, Y. Terashima, Y. Nishiyama, and M.G. Santoro Adv. Prostagland., Thromboxane Leukotriene Res. 19 1989 415
12. M. Fukushima, Y. Takeuchi, S. Kishimoto, S. Yamashita, K. Uetsuki, S. Shirakawa, M. Suzuki, K. Furuta, R. Noyori, H. Sasaki, Y. Kikuchi, T. Kita, T. Yamori, J. Sawada, M. Kojima, A. Hazato, S. Kurozumi, and M. Fukushima Anticancer. Drugs. 12 2001 221
13. M. Sasaki, S. Niimi, M. Akiyama, T. Tanaka, A. Hazato, S. Kurozumi, S. Fukushima, and M. Fukushima Cancer Res. 59 1999 3919
14. S. Fukushima, S. Kishimoto, Y. Takeuchi, and M. Fukushima Adv. Drug Deliv. Rev. 45 2000 65
15. G. Conti, P. Portincasa, S. Visalli, and C. Chezzi Virus Res. 75 2001 43
16. C. Rozero, A. Caratolli, A. De Marco, C. Amici, C. Giorgi, and M.G. Santoro J. Clin. Invest. 97 1996 1975
17. S.G. Harris, and R.P. Phipps Eur. J. Immunol. 31 2001 1098
18. E. Cernuda-Morollon, E. Pineda-Molina, F.J. Canada, and D. Perez-Sala J. Biol. Chem. 276 2001 35530
19. B.H. Rovin, L. Lu, and A. Cosio J. Am. Soc. Nephrol. 12 2001 1659
20. A. Rossi, G. Elia, and M.G. Santoro Proc. Natl. Acad. Sci. USA 94 1997 746
21. C. Amici, G. Belardo, A. Rossi, and M.G. Santoro J. Biol. Chem. 276 2001 28739
22. M. Suzuki, M. Mori, T. Niwa, R. Hirata, K. Furuta, T. Ishikawa, and R. Noyori J. Am. Chem. Soc. 119 1997 2376
23. R. Noyori, M. Mori, R. Hirata, Y. Shiga, T. Kokura, and M. Suzuki Pure Appl. Chem. 66 1994 1999
24. R. Noyori, and M. Suzuki Science. 259 1993 44
25. G. Venkata Ramana, and B. Venkateswara Rao Tetrahedron Lett. 44 2003 5103
26. J.K. Gallos, K.C. Damianou, and C.C. Dellios Tetrahedron Lett. 42 2001 5769
27. M. Seepersaud, and Y. Al-Abed Tetrahedron Lett. 41 2000 4291
28. V. Singh, and B. Thomas Tetrahedron 54 1998 3647
29. G. Mehta, and A. Srikrishna Chem. Rev. 97 1997 671
30. A. Srikrishna, and D.H. Dethe Org. Lett. 5 2003 2295
31. M. Ramaiah Synthesis 1984 529
32. E.M. Carreira E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis vol. III 1999 Springer Heidelberg 997 (Chapter 29)
33. D.D. Sternbach, and C.L. Ensinger J. Org. Chem. 55 1990 2725
34. K.B. Becker Tetrahedron 36 1980 1717
35. C. Kuhn, and J.-C. Florent Tetrahedron Lett. 39 1998 4247
36. C. Santelli-Rouvier Synthesis 1983 429
37. K.L. Habermas, S.E. Denmark, and T.K. Jones Org. React. (NY) 45 1994 1
38. S.E. Denmark B.M. Trost I. Fleming Comprehensive Organic Synthesis vol. 5 1991 Pergamon Oxford 751
39. M.A. Tius, J. Busch-Petersen, and M. Yamashita Tetrahedron Lett. 39 1998 4219
40. P.E. Harrington, T. Murai, C. Chu, and M.A. Tius J. Am. Chem. Soc. 124 2002 10091
41. W. Kirmse Angew. Chem. Int. Ed. 36 1997 1164
42. G.G.G. Manzardo, M. Karpf, and A.S. Dreiding Helv. Chim. Acta 69 1986 659
43. C. Aubert, O. Buisine, and M. Malacria Chem. Rev. 102 2002 813
44. L. Haughton, and J.M.J. Williams J. Chem. Soc., Perkin Trans. 1 2000 3335
45. B.M. Trost, and M.J. Krische Synlett 1998 1
46. I. Ojiwa, M. Tzamarioudaki, Z. Li, and R.J. Donovan Chem. Rev. 96 1996 635
47. N.E. Schore Chem. Rev. 88 1988 1081
48. B.M. Trost Angew. Chem. Int. Ed. 34 1995 259
49. I.U. Khand, G.R. Knox, P.L. Pauson, and W.E. Watts J. Chem. Soc., Chem. Commun. 1971 36
50. I.U. Khand, G.R. Knox, P.L. Pauson, W.E. Watts, and M.I. Foreman J. Chem. Soc., Perkin Trans. 1 1973 977
51. N.E. Schore Org. React. 40 1991 1
52. N.E. Schore B.M. Trost Comprehensive Organic Synthesis vol. 5 1991 Pergamon Oxford 1037
53. P. Magnus, and L.M. Principe Tetrahedron Lett. 26 1985 4851
54. V. Rautenstrauch, P. Mégard, J. Conesam, and W. Küster Angew. Chem. Int. Ed. 29 1990 1413
55. S.E. Gibson (née Thomas), and A. Stevenazzi Angew. Chem. Int. Ed. 42 2003 1800
56. M.R. Rivero, J. Adrio, and J.C. Carretero Eur. J. Org. Chem. 2002 2881
57. T. Sugihara, M. Yamaguchi, and M. Nishizawa Chem. Eur. J. 7 2001 1589
58. K.M. Brummond Tetrahedron 56 2000 3263
59. A.J. Fletcher, and S.D.R. Christie J. Chem. Soc., Perkin Trans. 1 2000 1657
60. Y.K. Chung Coord. Chem. Rev. 188 1999 297
61. O. Geis, and H-G. Schmalz Angew. Chem. Int. Ed. 37 1998 911
62. Y. Koga, T. Kobayashi, and K. Narasaka Chem. Lett. 1998 249
63. N. Jeong, S. Lee, and B.K. Sung Organometallics 17 1998 3642
64. N. Jeong, S.D. Seo, and J.Y. Shin J. Am. Chem. Soc. 122 2000 10220
65. P.A. Evans, and J.E. Robinson J. Am. Chem. Soc. 123 2001 4609
66. T. Kobayashi, Y. Koga, and K. Narasaka J. Organomet. Chem. 624 2001 73
67. C. Mukai, I. Nomura, K. Yamanishi, and M. Hanaoka Org. Lett. 4 2002 1755
68. K.H. Park, S.U. Son, and Y.K. Chung Tetrahedron Lett. 44 2003 2827
69. H. Cao, S.R. Mundla, and J.M. Cook Tetrahedron Lett. 44 2003 6165
70. N. Jeong, B.K. Sung, and Y.K. Choi J. Am. Chem. Soc. 122 2000 6771
71. K.M. Brummond, and D. Gao Org. Lett. 5 2003 3491
72. T. Morimoto, K. Fuji, K. Tsutsumi, and K. Kakiuchi J. Am. Chem. Soc. 124 2002 3806
73. T. Shibata, N. Toshida, and K. Takagi Org. Lett. 4 2002 1619
74. T. Shibata, N. Toshida, and K. Takagi J. Org. Chem. 67 2002 7446
75. P. Hong, T. Mise, and H. Yamazaki Bull. Chem. Soc. Jpn. 63 1990 247
76. I. Ojima, D.A. Fracchiolla, R.J. Donovan, and P. Banerji J. Org. Chem. 59 1994 7594
77. T. Shibata, and K. Takagi J. Am. Chem. Soc. 122 2000 9852
78. E. Negishi, and T. Takahashi Bull. Chem. Soc. Jpn. 71 1998 755
79. E. Negishi, and T. Takahashi Acc. Chem. Res. 27 1994 124
80. E. Negishi, S.J. Holmes, J.M. Tour, J.A. Miller, F.E. Cederbaum, D.R. Swanson, and T. Takahashi J. Am. Chem. Soc. 111 1989 3336
81. E. Negishi, D.R. Swanson, F.E. Cederbaum, and T. Takahashi Tetrahedron Lett. 28 1987 917
82. E. Negishi, S.J. Holmes, J.M. Tour, and J.A. Miller J. Am. Chem. Soc. 107 1985 2568
83. E. Negishi, F.E. Cederbaum, and T. Takahashi Tetrahedron Lett. 27 1986 2829
84. G. Agnel, Z. Owczarczyk, and E. Negishi Tetrahedron Lett. 33 1992 1543
85. E. Negishi, S. Ma, T. Sugihara, and Y. Noda J. Org. Chem. 62 1997 1922
86. P.A. Wender, and F.E. McDonald Tetrahedron Lett. 31 1990 3691
87. E. Negishi, J-L. Montchamp, L. Anastasia, A. Elizarov, and D. Choueiry Tetrahedron Lett. 39 1998 2503
88. T. Takahashi, Z. Xi, Y. Nishihara, S. Huo, K. Kasai, K. Aoyagi, V. Denisov, and E. Negishi Tetrahedron 53 1997 9123
89. T. Takahashi, Y. Li, F-Y. Tsai, and K. Nakajima Organometallics 20 2001 595
90. T. Takahashi, S. Huo, R. Hara, Y. Noguchi, K. Nakajima, and W-H. Sun J. Am. Chem. Soc. 121 1999 1094
91. Z. Xi, H.-T. Fan, S. Mito, and T. Takahashi J. Organomet. Chem. 682 2003 108
92. F.A. Hicks, N.M. Kablaoui, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 5881
93. F.A. Hicks, N.M. Kablaoui, and S.L. Buchwald J. Am. Chem. Soc. 118 1996 9450
94. S.C. Berk, R.B. Grossman, and S.L. Buchwald J. Am. Chem. Soc. 116 1994 8593
95. S.C. Berk, R.B. Grossman, and S.L. Buchwald J. Am. Chem. Soc. 115 1993 4912
96. R.B. Grossman, and S.L. Buchwald J. Org. Chem. 57 1992 5803
97. F.A. Hicks, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 7026
98. S.J. Sturla, and S.L. Buchwald J. Org. Chem. 64 1999 5547
99. F.A. Hicks, and S.L. Buchwald J. Am. Chem. Soc. 118 1996 11688
100. R. Aumann, and H.-J. Weidenhaupt Chem. Ber. 120 1987 23
101. B.E. Eaton, and B. Rollman J. Am. Chem. Soc. 114 1992 6245
102. A.J. Pearson, and A. Perosa Organometallics 14 1995 5178
103. A.J. Pearson, and R.A. Dubbert Organometallics 13 1994 1656
104. A.J. Pearson, and R.A. Dubbert J. Chem. Soc., Chem. Commun. 1991 202
105. T. Morimoto, N. Chatani, Y. Fukumoto, and S. Murai J. Org. Chem. 62 1997 3762
106. T. Kondo, N. Suzuki, T. Okada, and T. Mitsudo J. Am. Chem. Soc. 119 1997 6187
107. Y. Morisaki, T. Kondo, and T. Mitsudo Org. Lett. 2 2000 949
108. R. Aumann, and J. Uphoff Angew. Chem. Int. Ed. 26 1987 357
109. T.R. Hoye, and J.A. Suriano J. Am. Chem. Soc. 115 1993 1154
110. T.R. Hoye, and J.A. Suriano Organometallics 11 1992 2044
111. L. Jordi, A. Segundo, F. Camps, S. Ricart, and J.M. Moretó Organometallics 12 1993 3795
112. N. Jeong, and S.J. Lee Tetrahedron Lett. 34 1993 4027
113. H. Xiong, R.P. Hsung, L.L. Wei, C.R. Berry, J.A. Mulder, and B. Stockwell Org. Lett. 2 2000 2869
114. H. Cao, J. Flippen-Anderson, and J.M. Cook J. Am. Chem. Soc. 125 2003 3230
115. H. Cao, S.G. Van Ornum, and J.M. Cook Tetrahedron Lett. 41 2000 5313
116. G.P. Chiusoli Acc. Chem. Res. 6 1973 422
117. L. Cassar, G.P. Chiusoli, and M. Foà Tetrahedron Lett. 8 1967 285
118. L. Cassar, and G.P. Chiusoli Tetrahedron Lett. 6 1965 3295
119. F. Camps, J.M. Moretó, and L. Pagès Tetrahedron 15 1992 3147
120. F. Camps, J. Coll, J.M. Moretó, and J. Torras J. Org. Chem 54 1989 1969
121. A. Llebaria, and J.M. Moretó J. Organomet., Chem. 451 1993 1
122. F. Camps, J. Coll, J.M. Moretó, and J. Torras Tetrahedron Lett. 28 1987 4745
123. F. Camps, J. Coll, J.M. Moretó, and J. Torras Tetrahedron Lett. 26 1985 6397
124. L. Pagès, A. Llebaria, F. Camps, E. Molins, C. Miravitlles, and J.M. Moretó J. Am. Chem. Soc 114 1992 10449
125. F. Camps, A. Llebaria, J.M. Moretó, and L. Pagès Tetrahedron Lett. 33 1992 109
126. F. Camps, A. Llebaria, J.M. Moretó, and L. Pagès Tetrahedron Lett. 33 1992 113
127. J.M. Villar, A. Delgado, A. Llebaria, and J.M. Moretó Tetrahedron: Asymmetry 6 1995 665
128. J.M. Villar, A. Delgado, A. Llebaria, and J.M. Moretó Tetrahedron 52 1996 10525
129. K. Tamao, K. Kobayashi, and Y. Ito J. Am. Chem. Soc 110 1988 1286
130. K. Tamao, K. Kobayashi, and Y. Ito Synlett 1992 539
131. G. García-Gómez, and J.M. Moretó Eur. J. Org. Chem. 7 2001 1359
132. G. García-Gómez, and J.M. Moretó Chem. Eur. J. 7 2001 1503
133. G. García-Gómez, and J.M. Moretó J. Am. Chem. Soc. 121 1999 878
134. G.G. Gomez, X. Camps, A.J. Cayuela, and J.M. Moretó Inorg. Chim. Acta 296 1999 94
135. F. Vilaseca, L. Pagès, J.M. Villar, A. Llebaria, A. Delgado, and J.M. Moretó J. Organomet. Chem. 551 1998 107
136. W. Oppolzer Angew. Chem. Int. Ed. 28 1989 38
137. W. Oppolzer, T.H. Keller, M. Bedoya-Zurita, and C. Stone Tetrahedron Lett. 30 1989 5883
138. W. Oppolzer, M. Bedoya-Zurita, and C.Y. Switze Tetrahedron Lett. 29 1988 6433
139. W. Oppolzer, and C. Robyr Tetrahedron 50 1994 415
140. W. Oppolzer, J-Z. Xu, and C. Stone Helv. Chim. Acta 74 1991 465
141. W. Oppolzer Pure Appl. Chem. 62 1990 1941
142. N.C. Ihle, and C.H. Heathcock J. Org. Chem. 58 1993 560
143. R. Noyori Acc. Chem. Res. 12 1979 61
144. Y. Hayakawa, K. Yokoyama, and R. Noyori J. Am. Chem. Soc. 100 1978 1799
145. R. Noyori, Y. Hayakawa, H. Takaya, S. Murai, R. Kobayashi, and N. Sonoda J. Am. Chem. Soc. 100 1978 1759
146. R. Noyori, Y. Hayakawa, M. Funakura, and H. Takaya J. Am. Chem. Soc. 94 1972 7202
147. H.L. Stokes, L. Ni, J.A. Belot, and M.E. Welker J. Organomet. Chem. 487 1995 95
148. L. Ni, J.A. Belot, and M.E. Welker Tetrahedron Lett. 33 1992 177
149. M. Franck-Neumann, E.L. Michelotti, R. Simler, and J-M. Vernier Tetrahedron Lett. 33 1992 7361
150. M. Franck-Neumann, and J-M. Vernier Tetrahedron Lett. 33 1992 7365
151. E. Negishi, S. Ma, J. Amanfu, C. Copéret, J.A. Miller, and J.M. Tour J. Am. Chem. Soc. 118 1996 5919
152. E. Negishi, and J.M. Tour J. Am. Chem. Soc. 107 1985 8289
153. S.V. Gagnier, and R.C. Larock J. Am. Chem. Soc. 125 2003 4804
154. J.W. Herndon, and P.P. Patel Tetrahedron Lett. 38 1997 59
155. J.W. Herndon, D.K. Hill, and L.A. McMullen Tetrahedron Lett. 36 1995 5687
156. S.U. Tumer, J.W. Herndon, and L.A. McMullen J. Am. Chem. Soc. 114 1992 8394
157. J.W. Herndon, and S.U. Tumer Tetrahedron Lett. 30 1989 295
158. J.W. Herndon, S.U. Tumer, and W.F.K. Schmatter J. Am. Chem. Soc. 110 1988 3334
159. J.W. Herndon, and J.J. Matasi J. Org. Chem. 55 1990 786
160. J.W. Herndon, J. Zhu, and D. Sampedro Tetrahedron 56 2000 4985
161. A.K. Chatterjee, J.P. Morgan, R.H. Grubbs, and M. Scholl J. Am. Chem. Soc. 122 2000 3783
162. B.M. Trost, and C. Jiang Org. Lett. 5 2003 1563
163. A. Padwa J. Organomet. Chem. 617-618 2001 3
164. A. Padwa, D.J. Austin, and S.L. Xu J. Org. Chem. 57 1992 1330
165. T.R. Hoye Tetrahedron Lett. 32 1991 3755
166. T.R. Hoye, C.J. Dinsmore, D.S. Johnson, and P.F. Korkowski J. Org. Chem. 55 1990 4519
167. G. Deng, X. Tian, and J. Wang Tetrahedron Lett. 44 2003 587
168. K. Tanaka, and G.C. Fu J. Am. Chem. Soc. 123 2001 11492
169. K. Tanaka, and G.C. Fu J. Am. Chem. Soc. 124 2002 10296
170. G.R. Clark, and S. Thiensathit Tetrahedron Lett. 26 1985 2503