Generation and trapping of cyclopentenylidene gold species: Four pathways to polycyclic compounds

Journal of the American Chemical Society

Volumn 131, Issue 8, 2009, Pages 2993-3006

  Lemière, Gilles ^a   Gandon, Vincent ^a   Cariou, Kevin ^a   Hours, Alexandra ^a   Fukuyama, Takahide ^a   Dhimane, Anne Lise ^a   Fensterbank, Louis ^a   Malacria, Max ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

C-H INSERTION; CARBENES; COMPLEX MOLECULES; CYCLOPROPANATION; DFT COMPUTATIONS; GOLD COMPLEXES; NATURAL PRODUCTS; POLYCYCLIC COMPOUNDS; POLYCYCLIC FRAMEWORKS; TOTAL SYNTHESIS; VINYL ALLENES;

SYNTHESIS (CHEMICAL);

GOLD COMPOUNDS;

ALLENE DERIVATIVE; CARBENOID; CARBON; GOLD; GOLD COMPLEX; HYDROGEN; NATURAL PRODUCT; POLYCYCLIC HYDROCARBON; PROTON;

ARTICLE; CYCLOPROPANATION; FOURIER TRANSFORMATION; SPECIES; SYNTHESIS;

EID: 67749084445     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja808872u     Document Type: Article

References (167)

1. The rendition as gold-carbene or gold-stabilized carbocation is a matter of debate that is beyond the scope of this article, see: (a) Fürstner, A.; Morency, L. Angew. Chem., Int. Ed. 2008, 47, 5030.
2. (b) Jiménez-Núñez, E.; Claverie, C. K.; Bour, C.; Cárdenas, D. J.; Echavanen, A. M. Angew. Chem., Int. Ed. 2008, 47, 7892.
3. (c) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2008, 47, 6754.
4. For recent reviews on gold-mediated homogeneous catalysis, see: (a) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239.
5. (b) Arcadi, A. Chem. Rev. 2008, 108, 3266.
6. (c) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326.
7. (d) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351.
8. (e) Muzart, J. Ttrahedron 2008, 64, 5815.
9. (f) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395.
10. (g) Skouta, R.; Lie, C.-J. mrahedron 2008, 64, 4917.
11. (h) Shen, H. C. Tetrahedron 2008, 64, 3885.
12. (i) Hashmi, S. A. Chem. Rev. 2007, 107, 3180.
13. (j) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395.
14. (k) Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
15. (l) Amijs, C. H. M.; Ferrer, C.; Echavarren, A. M. Chem. Commun. 2007, 698.
16. (m) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333.
17. (n) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 248, 2271.
18. (o) Malacria, M.; Goddard, J.-P.; Fensterbank, L. In Comprehensive Organometallic Chemistry, 3rd ed.: Crabtree, R., Mingos, M., Eds.; Elsevier: Amsterdam, 2006; Vol. 10, Chapter 10.07, p 299.
19. (p) Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem., Int. Ed. 2006, 45, 7896.
20. (q) Widenhoefer, R. A.; Han, X. Eur. J. Org. Chem. 2006, 4555.
21. For selected examples of generation and trapping of platinum or gold carbenes from alkynes, see: (a) Takaya, J.; Udagawa, S.; Kusama, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2008, 46, 4906.
22. (b) Leseurre, L.; Toullec, P. Y.; Genêt, J.-P.; Michelet, V. Org. Lett. 2008, 9, 4049.
23. (c) Kirsch, S. F. Synthesis 2008, 3183.
24. (d) Li, G.; Zhang, L. Angew. Chem., Int. Ed. 2007, 46, 5156.
25. (e) Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 4160.
26. (f) Cabello, N.; Jiménez-Nùñez, E.; Buñuel, E.; Cárdenas, D. J.; Echavarren, A. M. Eur. J. Org. Chem. 2007, 4217.
27. (g) Genin, E.; Leseurre, L.; Toullec, P. Y.; Genêt, J.-P.; Michelet. V. Synlett 2007, 1780.
28. (h) Amijs, C. H. M.; Ferrer, C.; Echavanen, A. M. Chem. Commun. 2007, 698.
29. (i) Toullec, P. Y.; Genin, E.; Leseune, L.; Genêt, J.-P.; Michelet, V. Angew. Chem., Int. Ed. 2006, 45, 7427.
30. (j) Nieto-Oberhuber, C.; López. S.; Jiménez- Núñez, E.; Echavanen, A. M. Chem. Eur. J. 2006, 12, 5916.
31. (k) Nieto-Oberhuber, C.; López, S.; Muñoz, M. P.; Buñuel. E.; Cárdenas, D. J.; Echavanen, A. M. Chem.-Eur. J. 2006, 11, 1694.
32. (l) Nieto-Oberhuber, C.; López, S.; Muñoz. M. P.; Cárdenas, D. J.; Buñuel. E.; Nevado, C.; Echavanen, A. M. Angew. Chem., Int. Ed. 2005, 44, 6146.
33. (m) Zhang, L.; Kozmin, S. J. Am. Chem. Soc. 2005, 127, 6962.
34. (n) Nevado, C; Charruault, L.; Michelet, V.; Nieto-Oberhuber, C.; Muñoz, M. C.; Méndez, M.; Rager, M.-N.; Genêt, J.-P.; Echavanen, A. M. Eur. J. Org. Chem. 2003, 706.
35. (o) Méndez. M; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavanen, A. M. J. Am. Chem. Soc. 2001, 123, 10511.
36. (a) Bruneau. C. Angew. Chem., Int. Ed. 2005, 44, 2328. For representative examples, see:
37. (b) Boyer, F.-D.; Le Goff, X.; Hanna, I. J. Org. Chem. 2008, 73, 5163.
38. (c) Moreau, X.; Goddard, J.-P.; Bernard, M.; Lemière, G.; López-Romero, J. M.; Mainetti, E.; Marion, N.; Mouriès, V.; Thorimbert. S.; Fensterbank, L.; Malacria. M. Adv. Synth. Catal 2008, 350, 43.
39. (d) Kim, S. M.; Park, J. H.; Choi, S. Y.; Chung, Y. K. Angew. Chem., Int. Ed. 2007, 46, 6172.
40. (e) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. 2006, 45, 2901.
41. (f) Fürstner, A.; Hannen, P. Chem. Eur. J. 2006, 12, 3006.
42. (g) López, S.; Herrero-Gomez, E.; Perez-Galan, P.; Nieto-Oberhuber, C.; Echavanen, A. M. Angew. Chem., Int. Ed. 2006, 45, 6022.
43. (h) Fürstner, A.; Davies, P. W.; Gress, T. J. Am. Chem. Soc. 2005, 127, 8244.
44. (i) Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavanen, A. M. Angew. Chem., Im. Ed. 2004, 43, 2402.
45. (j) Hanak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti. E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
46. (k) Blaszykowski, C.; Hanak, Y.; Goncalves, M.-H.; Cloarec, J.-M.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Org. Lett. 2004, 6, 3771.
47. (l) Fürstner, A.; Schlecker, A. Chem. Eur. J. 2008, 14, 9181.
48. With the exception of allenyl acetates, which can be easily generated from propargyl acetates by 3,3-rearrangement, see: (a) Correa, A.; Marion, N.; Fensterbank, L.; Malacria, M.; Nolan, S. P.; Cavallo, L. Angew. Chem., Int. Ed. 2008, 47, 718.
49. (b) Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750.
50. (c) Marco-Contelles, J.; Soriano, E. Chem. Eur. J. 2007, 13, 1350, and references therein.
51. (a) Sromek, A. W.; Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500.
52. (b) Dudnik, A. S.; Sromek, A. W.; Rubina, M.; Kim, J. T.; Kel'in, A. V.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 1440.
53. (c) Funami, H.; Kusama, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2007, 46, 909.
54. (d) Lee, J. H.; Toste, F. D. Angew. Chem., Int. Ed. 2007, 46, 912.
55. (e) Huang, X.; Zhang, L. J. Am. Chem. Soc. 2007. 129, 6398.
56. (f) Trillo, B.; López, F.; Gulías, M.; Castedo, L.; Mascareñas. J. L. Angew. Chem., Int. Ed. 2008, 47, 951.
57. (g) Buzas, A.; Gagosz, F. J. Am. Chem. Soc 2006, 128, 12614.
58. (h) Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 8414.
59. (i) Crone, B.; Kirsch, S. F. Chem. Eur. J. 2008, 14, 3514.
60. (j) Bhunia, S.; Liu, R.-S. J. Am. Chem. Soc. 2008, 130, 16488.
61. (a) Grimaldi, J.; Bertrand, M. Tetrahedron Lett. 1969, 38, 3269.
62. (b) Grimaldi, J.; Bertrand, M. Bull. Soc. Chim. Fr. 1971, 3, 957.
63. (c) Roumestant, M. L.; Malacria, M.; Gore, J.; Grimaldi, J.; Bertrand, M. Synthesis 1976, 755.
64. (d) Malacria, M.; Roumestant, M. L. Tetrahedron 1977, 33, 2813.
65. (e) Doutheau, A.; Gore, J.; Malacria, M. Tetrahedron 1977, 33, 2393.
66. (f) Malacria, M.; Goré, J. J. Org. Chem. 1979, 44, 885.
67. (g) Malacria, M.; Goré, J. Tetrahedron Lett. 1979, 52, 5067.
68. For gold-catalyzed cycloisomerizations of higher eneallene homologues, see: Tarselli, M. A.; Chianese. A. R.; Lee, S. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2007, 46, 6670.
69. For recent reviews on Nazarov cyclization, see: (a) Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577.
70. (b) Pellissier, H. Tetrahedron 2005, 61, 6479.
71. (c) Tius, M. A. Eur. J. Org. Chem. 2005, 2193
72. See also. Habermas, K. L.; Denmark, S. E.; Jones, T. K. Org. React. (N.Y.) 1994, 45, 1-158.
73. For a seminal work on transition-metal mediated activation of vinyl alienes, see: (a) Delbecq, F.; Goré, J. Tetrahedron Lett. 1976, 38, 3459.
74. (b) Baudouy, R.; Delbecq. F.; Gore, J. Tetrahedron 1980, 36, 189.
75. For gold-catalyzed teansformations involving Nazarov cyclizations, see: (a) Lin, G.-Y.; Li, C.-W.; Hung, S.-H.; Liu. R.-S. Org. Lett. 2008, 10, 5059.
76. (b) Lin, C.-C.; Teng, T.-M.; Tsai, C.-C.; Liao, H.-Y.; Liu, R.-S. J. Am. Chem. Soc. 2008, 130, 16417.
77. Angular triquinanes have been prepared in several steps using goldcatalysis, but not directly: Sethofer, S. G.; Staben, S. T.; Hung, O. Y.; Toste, F. D. Org. Lett. 2008, 10, 4315.
78. (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671.
79. (b) Pihko, A. J.; Koskinen, A. M. P. Tetrahedron 2005, 61, 8769.
80. For two preliminary communications, see: (a) Lemière, G.; Gandon, V.; Cariou, K.; Fukuyama, T.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Org. Lett. 2007, 9, 2207.
81. (b) Gandon, V.; Lemière, G.; Hours, A.; Fensterbank, L.; Malacria, M. Angew. Chem., Int. Ed. 2008, 47, 7534.
82. Simultaneously to our work, Toste et al. disclosed an intramolecular variant of this transformation, see ref 6d.
83. Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492.
84. See inter alia ref 6h and (a) Marion, N.; Díez-González, S.; De Fremont, P.; Noble, A. R.; Nolan, S. P. Angew. Chem., Int. Ed. 2006, 45, 3647.
85. (b) Cariou, K.; Mainetti, E.; Fensterbank, L.; Malacria, M. Tetrahedron 2004, 60, 9745.
86. (c) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280.
87. (d) Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546.
88. (e) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; MarcoContelles, J. J. Am. Chem. Soc 2004, 126, 3408, and references therein.
89. 6 alone were able to promote this reaction. The starting material was recovered intact.
90. CCDC 684838, see Supporting Information of ref 14b.
91. For reports on bent-allenes and their transition metal complexes, see: (a) Dvker, C. A.; Lavallo, V.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 3206.
92. (b) Kaufhold, O.; Hahn, F. E. Angew. Chem., Int. Ed. 2008, 47, 4057.
93. (c) Fürstner, A.; Alcarazo, M.; Goddard, R.; Lehmann, C. W. Angew. Chem., Int. Ed. 2008, 47, 3210.
94. (d) Tonner, R.; Frenking, G. Angew. Chem., Int. Ed. 2007, 46, 8695.
95. (e) Yamaguchi, T.; Yamamoto, Y.; Kinoshita, D.; Akiba, K.-a.; Zhang, Y.; Reed, C. A.; Hashizume, D.; Iwasaki, F. J. Am. Chem. Soc. 2008, 130, 6894.
96. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129.
97. Henero-Gomez, E.; Nieto-Oberhuber, C.; López, S.; Benet-Buchholz, J.; Echavanen, A. M. Angew. Chem., Int. Ed. 2006, 45, 5455.
98. The fact that the formation of the decaline system 41 requires higher temperature compared to 38 has been previously observed, see:(a) Snider, B. B.;
99. Burbaum, B. W. J. Org. Chem. 1983, 48, 4370.
100. (b) Okamura, W. H.; Curtin, M. L. Synlett 1990, 1.
101. Examples of Diels-Alder reaction involving vinyl alienes as diene are scarce; for a seminal work, see: (a) Bertrand, M.; Grimaldi, J.; Waegell, B. Chem. Commun. (London) 1968, 19, 1141.
102. (b) Marcel, B.; Grimaldi, J.; Waegell, B. Bull. Soc Chim. Fr. 1971, 3, 962, This reaction has been used as key-step in the total syndiesis of natural products: (c) Deutsch, E. A.;
103. Snider, B. B. J. Org. Chem. 1982, 47, 2682.
104. (d) Keck, G. E.; Kachensky. D. F. J. Org. Chem. 1986, 51, 2487.
105. (e) Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791.
106. (f) Gibbs, R. A.; Okamura, W. H. J. Am. Chem. Soc. 1988, 110, 4062.
107. (g) Gibbs, R. A.; Bartels, K.; Lee, R. W. K.; Okamura, W. H. J. Am. Chem. Soc. 1989, 111, 3717.
108. Gaussian 03, Revision D.02, Frisch, M. J.,; Gaussian, Inc.: Wallingford CT, 2004.
109. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
110. (a) Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
111. (b) Hehre, W. J.; Ditchfield, R.; Pople, J. A. Chem. Phys. 1972, 56, 2257.
112. (c) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
113. (d) Hariharan, P. C.; Pople, J. A. Mol Phys. 1974, 27, 209.
114. (e) Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163.
115. http://www.chemcraftprog.com.
116. For another type of gold-catalyzed [4 + 2] cycloaddition, see: Nieto-Oberhuber, C.; Pérez-Galán, P.; Herrero-Gómez, E.; Lauterbach, T.; Rodríguez, C.; López, S.; Bour, C.; Rosellón, A.; Cárdenas, D. J.; Echavanen, A. M. J. Am. Chem. Soc. 2008, 130, 269.
117. For a computational study dealing with hetero Diels-Alder reaction of vinyl allenes and aldehydes, see: Regás, D.; Ruiz, J. M.; Afonso, M. M.; Palenzuela, J. A. J. Org. Chem. 2006, 71, 9153.
118. For the concept of slippage, see: (a) Eisenstein, O.; Hoffmann, R J. Am. Chem. Soc. 1981, 103, 4308. See also:
119. (b) Senn, H. M.; Blöchl, P. E.; Togni, A. J. Am. Chem. Soc. 2000, 122, 4098.
120. As shown by Gevorgyan et al., the H-migration could also be assisted by traces of water. This might explain why the switch over could not be reproduced computationally. See: Xia, Y.; Dudnik, A. S.; Gevorgyan, V.; Li, Y. J. Am. Chem. Soc. 2008, 130, 6940.
121. (a) Paquette, L. A.; Doherty, A. M. Recent Synthetic Developments in Polyquinane Chemistry; Springer-Verlag: New York, 1987.
122. (b) Devon, T. K.; Scott, A. I. Handbook of Naturally Occuring Compounds; Academic Press: New York, 1972; Vol. II, 180.
123. (c) Comer, F. W.; Trotter, J. J. Chem. Soc. B 1966, 1, 1.
124. Ayanoglu, E.; Gebreyesus, T.; Beechan, C. M.; Djerassi, C.; Kaisin, M. Tetrahedron Lett. 1978, 1671.
125. (a) Kaisin, M.; Sheikh. Y. M.; Durham, L. J.; Djerassi, C. Tetrahedron Lett. 1974, 2239.
126. (b) Kaisin, M.; Braekman, J. C.; Daloze, D.; Tursch, B. Tetrahedron 1985, 41, 1067.
127. (c) Monis, L. A.; Jaspars, M.; Adamson, K.; Woods, S.; Wallace, H. M. Tetrahedron 1998, 54, 12953.
128. (d) Chang, C.-H.; Wen. Z.-H.; Wang, S.-K.; Duh, C. -Y. J. Nat. Prod. 2008, 71, 619.
129. (a) Little, R. D.; Carroll, G. L. Tetrahedron Lett. 1981, 22, 4389.
130. (b) Stevens, K. E.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 4393.
131. (c) Birch, A. M.; Pattenden, G. Tetrahedron Lett. 1982, 23, 991.
132. (d) Fujita, T.; Ohtsuka, T.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1982, 23, 4091.
133. (e) Oppolzer, W.; Battig, K. Tetrahedron Lett. 1982, 23, 4669.
134. (t) Huguet, J.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1982, 65, 2413.
135. (g) Mehta, G.; Reddy, D. S.; Murty, A. N. Chem. Soc., Chem. Commun. 1983, 824.
136. (h) Piers, E.; Karunaratne, V. Can. Chem. 1984, 62, 629.
137. (i) Crisp, G. T.; Scott, W. J.; Stille, J. K. J Am. Chem. Soc. 1984, 106, 7500.
138. (j) Liu, H. J.; Kulkarni, M. G. Tetrahedron Lett. 1985, 26, 4847.
139. (k) Curran, D. P.; Chen, M.-H. Tetrahedron Lett. 1985, 26, 4991.
140. (l) Stille, J. R.; Grabbs, R. H. J. Am. Chem. Soc. 1986, 108, 855.
141. (m) Iyoda, M.; Kushida, T.; Kitami, S.; Oda, M. J. Chem. Soc., Chem. Commun. 1987, 1607.
142. (n) Uyehara, T.; Furuta, T.; Akamatsu, M.; Kato, T.; Yamamoto, Y. J. Org. Chem. 1989, 54, 5411.
143. (o) Wang, Y.; Mukherjee, D.; Birnev, D.; Houk, K. N. J. Org. Chem. 1990, 55, 4504.
144. (p) Ihara, M.; Suzuki, T.; Katogi, M.; Taniguchi, N.; Fukumoto, K. Chem. Soc., Chem. Commun. 1991, 646.
145. (q) Gambacorta, A.; Fabrizi, G.; Bovicelli, P. Tetrahedron Lett. 1992, 48, 4459.
146. (r) Shono, T.; Kise, N.; Fujimoto, T.; Tominaga, N.; Morita, H. Tetrahedron Lett. 1992, 57, 7175.
147. (s) Balme, G.; Bouyssi, D. Tetrahedron 1994, 50, 403.
148. (t) Tanaka, K.; Ogasawara, K. Chem. Commun. 1996, 1839.
149. (u) Singh, V.; Prathap, S.; Porinchu, M. mrahedron Lett. 1997, 38, 2911.
150. (v) Samajdar, S.; Patra, D.; Ghosh, S. Tetrahedron 1998, 54, 1789.
151. (a) Meyers, A. I.; Bienz, S. J. Org. Chem. 1990, 55, 791.
152. (b) Sonawane, H. R.; Nanjundian, B. S.; Shah, V. G.; Kulkarni, D. G.; Ahuja, J. R. Tetrahedron Lett. 1991, 32, 1107.
153. (e) Ohshima, T.; Kagechika, K.; Adachi, M.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1996, 118, 7108.
154. 4.
155. CCDC 706846.
156. For an example of such transformation, see:Taber, D. F.; Nakajima, K.; Xu, M.; Rheingold, A. L. J. Org. Chem. 2002, 67, 4501
157. See also. Toyota, M.; Nishikawa, Y.; Motoki, K.; Yoshida, N.; Fukumoto, K. Tetrahedron 1993, 49, 11189.
158. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 16, 1574.
159. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
160. (a) Saitoh, F.; Mori, M.; Okamura, K.; Date, T. Tetrahedron 1995, 51, 4439.
161. (b) Grieco, P. A.; Brandes, E. B.; McCann, S.; Clark, J. D. J. Org. Chem. 1989, 54, 5849.
162. CCDC 706847.
163. (a) Doyle, M. P. Chem. Rev 1986, 86, 919.
164. (b) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
165. For selected examples, see: Rh: (a) Shi, W.; Zhang, B.; Zhang, J.; Liu, B.; Zhang, S.; Wang, J. Org. Lett. 2005, 7, 3103; Cu:
166. (b) Yates, P.; Danishefsky, S. J. Am. Chem. Soc. 1962, 84, 879;
167. (c) Wrobel, J.; Takahashi, K.; Honkan, V.; Lannove, G.; Cook, J. M. J. Org. Chem. 1983, 48, 141.