Highly diastereo- and regioselective transition metal-catalyzed additions of metal hydrides and bimetallic species to cyclopropenes: Easy access to multisubstituted cyclopropanes

Journal of Organic Chemistry

Volumn 72, Issue 23, 2007, Pages 8910-8920

  Trofimov, Alexander ^a   Rubina, Marina ^a   Rubin, Michael ^a   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPENES; CYCLOPROPYLMETALS; METAL HYDRIDES;

CATALYST ACTIVITY; HYDRIDES; REGIOSELECTIVITY; TRANSITION METALS;

ADDITION REACTIONS;

CYCLOALKENE; CYCLOPROPANE DERIVATIVE; CYCLOPROPENE DERIVATIVE; GERMANE DERIVATIVE; GERMANIUM DERIVATIVE; METAL DERIVATIVE; METAL HYDRIDE; SILANE DERIVATIVE; SILYLTIN DERIVATIVE; TIN DERIVATIVE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 35948955856     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701855c     Document Type: Article

References (126)

1. For a review, see: Rubina, M.; Gevorgyan, V. Tetrahedron 2004, 60, 3129.
2. (a) Luithle, J. E. A.; Pietruszka, J. J. Org. Chem. 1999, 64, 8287.
3. (b) Pietruszka, J. Chem. Rev. 2003, 103, 1051.
4. Paquette, L. A. Chem. Rev. 1986, 86, 733.
5. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117.
6. (a) Corey, E. J.; De, B. J. Am. Chem. Soc. 1984, 106, 2735.
7. (b) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213.
8. (c) Falck, J. R.; Mekonnen, B.; Yu, J.; Lai, J.-Y. J. Am. Chem. Soc. 1996, 118, 6096.
9. (d) Wakamatsu, H.; Isono, N.; Mori, M. J. Org. Chem. 1997, 62, 8917.
10. (e) Heureux, N.; Marchant, M.; Maulide, N.; Berthon-Gelloz, G.; Hermans, C.; Hermant, S.; Kiss, E.; Leroy, B.; Wasnaire, P.; Marko, I. E. Tetrahedron Lett. 2004, 46, 79.
11. (a) Piers, E.; Jean, M.; Marrs, P. S. Tetrahedron Lett. 1987, 28, 5075.
12. (b) Wiedemann, S.; Rauch, K.; Savchenko, A.; Marek, I.; de Meijere, A. Eur. J. Org. Chem. 2004, 3, 631.
13. (a) Pohmakotr, M.; Sithikanchanakul, S. Synth. Commun. 1989, 19, 3011.
14. (b) Arney, B. E.; Wilcox, K.; Campbell, E.; Gutierrez, M. O. J. Org. Chem. 1993, 58, 6126.
15. (c) Banwell, M. G.; Cameron, J. M.; Collis, M. P.; Gravatt, G. L. Aust. J. Chem. 1997, 50, 395.
16. (d) Angelaud, R.; Landais, Y. Tetrahedron 2000, 56, 2025.
17. (a) Lautens, M.; Delanghe, P. H. M. J. Org. Chem. 1992, 57, 798.
18. (b) Wakamatsu, H.; Isono, N.; Mori, M. J. Org. Chem. 1997, 62, 8917.
19. (c) France, M. B.; Milojevich, A. K.; Stitt, T. A.; Kim, A. J. Tetrahedron Lett. 2003, 44, 9287.
20. (d) Gawley, R. E.; Narayan, S. Chem. Commun. 2005, 40, 5109.
21. (e) Sharma, V. B.; Jain, S. L.; Sain, B. Catal. Commun. 2006, 7, 454.
22. Barluenga, J.; Fananas, F. J.; Sanz, R.; Marcos, C. Org. Lett. 2002, 4, 2225.
23. For the preparation of cyclopropenes, see: (a) Doyle, M. P.; Protopopova, M.; Muller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492.
24. (b) Davies, H. M. L.; Houser, J. H.; Thornley, C. J. Org. Chem. 1995, 60, 7529.
25. (c) Lou, Y.; Horikawa, M.; Kloster, R. A.; Hawryluk, N. A.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8916.
26. (d) Davies, H. M. L.; Lee, G. H. Org. Lett. 2004, 6, 1233.
27. (e) Rubin, M.; Gevorgyan, V. Synthesis 2004, 5, 796.
28. (f) Lou, Y.; Remarchuk, T. P.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 14223.
29. (g) Panne, P.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 22.
30. For discussion on strain energy in small rings, see: Bach, R. D.; Dmitrenko, J. J. Am. Chem. Soc. 2004, 126, 4444.
31. For reviews, see: (a) Fox, J. M.; Yan, N. Curr. Org. Chem. 2005, 9, 719.
32. (b) Rubin, M.; Rubina, M.; Gevorgyan, V. Synthesis 2006, 8, 1221.
33. For additions of Grignards, see: (c) Liao, L.; Fox, J. M. J. Am. Chem. Soc. 2002, 124, 14322.
34. (d) Liao, L.; Zhang, F.; Yan, N.; Golen, J. A.; Fox, J. M. Tetrahedron 2004, 60, 1803.
35. (e) Liu, X.; Fox, J. M. J. Am. Chem. Soc. 2006, 128, 5600.
36. (f) Simaan, S.; Marek, I. Org. Lett. 2007, 9, 2569.
37. For additions of organoindium reagents, see: (g) Araki, S.; Nakano, H.; Subburaj, K.; Hirashita, T.; Shibutani, K.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron Lett. 1998, 39, 6327.
38. (h) Araki, S.; Shiraki, F.; Tanaka, T.; Nakano, H.; Subburaj, K.; Yamamura, H.; Kawai, M. Chem.-Eur. J. 2001, 7, 2784.
39. (i) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033.
40. (j) Araki, S.; Tanaka, T.; Hirashita, T.; Setsune, J. Tetrahedron Lett. 2003, 44, 8001.
41. For additions of organozinc reagents, see: (k) Stoll, A. T.; Negishi, E. Tetrahedron Lett. 1985, 26, 5671.
42. For additions of alkynes, see: (l) Yin, J.; Chisholm, J. D. Chem. Commun. 2006, 6, 632.
43. For hydroallumination, see: (m) Baldwin, J. E.; Villarica, K. A. J. Org. Chem. 1995, 60, 186.
44. (n) Gajewski, J. J.; Olson, L. P.; Willcott, M. R., III. J. Am. Chem. Soc. 1996, 118, 299.
45. For additions of heteroatom nucleophiles, see: (o) Martinez-Grau, A.; Blasco, J. M.; Ferrito, R.; Espinosa, J. F.; Mantecon, S.; Vaquero, J. J. Arkivoc 2005, 9, 394.
46. For reduction of cyclopropene, see: (p) Zohar, E.; Marek, I. Org. Lett. 2004, 6, 341.
47. For formation of cyclopropylpalladacycles, see: (q) Hashmi, A. S. K.; Naumann, F.; Boite, M. Organometallics 1998, 17, 2385.
48. For cycloadditions, see: (r) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett. 2001, 3, 3193.
49. (s) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849.
50. (t) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570.
51. (u) Pallerla, M. K.; Fox, J. M. Org. Lett. 2005, 7, 3593.
52. For isomerization to methylenecyclopropane, see: (v) Simaan, S.; Masarwa, A.; Bertus, P.; Marek, I. Angew. Chem., Int. Ed. 2006, 45, 3963.
53. (w) Yang, Z.; Xie, X.; Fox, J. M. Angew. Chem., Int. Ed. 2006, 45, 3960.
54. For cycloisomerization of cyclopropenes, see: (a) Tomilov, Y. V.; Shapiro, E. A.; Protopopova, M. N.; Ioffe, A. I.; Dolgii, I. E.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1985, 3, 631.
55. (b) Cho, S. H.; Liebeskind, L. S. J. Org. Chem. 1987, 52, 2631.
56. (c) Davies, H. M. L.; Romines, K. R. Tetrahedron 1988, 44, 3343.
57. (d) Padwa, A.; Kulkarni, Y. S.; Terry, L. W. J. Org. Chem. 1990, 55, 2478.
58. (e) Mueller, P.; Pautex, N.; Doyle, M. P.; Bagheri, V. Helv. Chim. Acta 1990, 73, 1233.
59. (f) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1991, 56, 6971.
60. (g) Müller, P.; Gränicher, C. Helv. Chim. Acta 1993, 76, 521.
61. (h) Müller, P.; Gränicher, C. Helv. Chim. Acta 1995, 78, 129.
62. (i) Ma, S.; Zhang, J. J. Am. Chem. Soc. 2003, 125, 12386.
63. For additions with ring opening of cyclopropenes, see: (j) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297.
64. Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566.
65. For enantioselective hydroboration of cyclopropenes, see: (a) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198.
66. For enantioselective hydrostannation of cyclopropenes, see: (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688.
67. For reviews, see: (a) Smith, N. D.; Mancuso, J.; Lautens, M. Chem. Rev. 2000, 100, 3257.
68. (b) Beletskaya, I.; Moberg, C. Chem. Rev. 2006, 106, 2320.
69. Kikkawa, S.; Nomura, M.; Hosoya, K. Nippon Kagaku Kaishi 1973, 6, 1130.
70. (a) Nakamura, E.; Machii, D.; Inubushi, T. J. Am. Chem. Soc. 1989, 111, 6849.
71. (b) Yamago, S.; Ejiri, S.; Nakamura, E. Chem. Lett. 1994, 1889.
72. (a) Paquette, L. A.; Uchida, T.; Gallucci, J. C. J. Am. Chem. Soc. 1984, 106, 335.
73. (b) Paquette, L. A.; Hoppe, M.; Johnston, L. J.; Ingold, K. U. Tetrhedron Lett. 1986, 27, 411.
74. (c) Walborsky, H. M.; Topolski, M. J. Org. Chem. 1992, 57, 370.
75. (a) Mushak, P.; Battiste, M. A. J. Organomet. Chem. 1969, 17, 46.
76. (b) Fiato, R. A.; Mushak, P.; Battiste, M. A. Chem. Commun. 1975, 21, 869.
77. (c) Battiste, M. A.; Friedrich, L. E.; Fiato, R. A. Tetrahedron Lett. 1975, 1, 45.
78. (d) Lukin, K. A.; Zefirov, N. S. Zh. Org. Khim. 1990, 26, 289.
79. (e) Donovan, B. T.; Hughes, R. P.; Spara, P. P.; Rheingold, A. L. Organometallics 1995, 14, 489.
80. (a) Baird, R. L.; Weigert, F. J.; Shapley, J. R. J. Am. Chem. Soc. 1970, 92, 6630.
81. (b) Binger, P.; Schroth, G.; McMeeking, J. Angew. Chem., Int. Ed. 1974, 13, 465.
82. (c) Binger, P.; McMeeking, J.; Schuchardt, U. Chem. Ber. 1980, 113, 2372.
83. (d) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 1649.
84. (e) Binger, P.; Buech, H. M.; Benn. R.; Mynott, R. Angew. Chem., Int. Ed. 1982, 21, 62.
85. Rush, S.; Reinmuth, A.; Risse, W. Macromolecules 1997, 30, 7375.
86. For examples on directing effect in hydrostannation, see: (a) Betzer, J.-F.; Delaloge, F.; Muller, B.; Pancrazi, A.; Prunet, J. J. Org. Chem. 1997, 62, 7768.
87. (b) Rice, M. B.; Whitehead, S. L.; Horvath, C. M.; Muchnij, J. A.; Maleczka, R. E., Jr. Synthesis 2001, 10, 1495.
88. MOP = (RS)-2-(diphenylphosphino)-2′-methoxy-1,1′-binaphtyl.
89. Marciniec, B. Hydrosilylation and Related Reactions of Silicon Compounds: Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; 2002; Vol. 1, p 491.
90. For an example of Lewis acid mediated reactions of cyclopropylsilanes with electrophiles, see: Schaumann, E.; Mergardt, B. J. Chem. Soc., Perkin Trans. 1 1989, 7, 1361.
91. For reactions of cyclopropylsilanes involving generation of cyclopropylanions, see: (a) Blankenship, C.; Wells, G. J.; Paquette, L. A. Tetrahedron 1988, 44, 4023.
92. (b) Ohno, M.; Tanaka, H.; Komatsu, M.; Ohshiro, Y. Synlett 1991, 12, 919.
93. (c) Shibuya, A.; Pietz, S.; Taguchi, T. Tetrahedron Lett. 1997, 38, 5537.
94. (d) Adams, D. J.; Blake, A. J.; Cooke, P. A.; Gill, C. D.; Simpkins, N. S. Tetrahedron 2002, 58, 4603.
95. (e) Wang, Z.; Silverman, R. B. J. Enzyme Inhibit. Med. Chem. 2004, 19, 293.
96. See, for example: (a) Angelaud, R.; Landais, Y.; Maignan, C. Tetrahedron Lett. 1995, 36, 3861.
97. (b) Yamamura, Y.; Toriyama, F.; Kondo, T.; Mori, A. Tetrahedron: Asymmetry 2002, 13, 13.
98. (c) Begis, G.; Sheppard, T. D.; Cladingboel, D. E.; Motherwell, W. B.; Tocher, D. A. Synthesis 2005, 19, 3186.
99. See, for example: (a) Mizojiri, R.; Urabe, H.; Sato, F. J. Org. Chem. 2000, 65, 6217.
100. (b) Honda, M.; Mita, T.; Nishizawa, T.; Sano, T.; Segi, M.; Nakajima, T. Tetrahedron Lett. 2006, 47, 5751.
101. See, for example: (a) Ir: Cipot, J.; Ferguson, M. J.; Stradiotto, M. Inorg. Chim. Acta 2006, 359, 2780.
102. (b) Ni: Boucher, S.; Zargarian, D. Can. J. Chem. 2006, 84, 233.
103. (c) Rh: Rivera, G.; Crabtree, R. H. J. Mol. Catal. A: Chem. 2004, 222, 59.
104. (d) Goikhman, R.; Milstein, D. Chem. - Eur. J. 2005, 11, 2983.
105. (e) Imlinger, N.; Wurst, K.; Buchmeiser, M. R. J. Organomet. Chem. 2005, 690, 4433.
106. (f) Muraoka, T.; Matsuda, I.; Itoh, K.; Ueno, K. Organometallics 2007, 26, 387.
107. (g) Pd: Sui-Seng, C.; Groux, L. F.; Zargarian, D. Organometallics 2006, 25, 571.
108. For Pt-catalyzed hydrosilylation, see for example: (a) Marko, I. E.; Sterin, S.; Buisine, O.; Berthon, G.; Michaud, G.; Tinant, B.; Declercq, J.-P. Adv. Synth. Catal. 2004, 346, 1429.
109. (b) Berthon-Gelloz, G.; Buisine, O.; Briere, J. F.; Michaud, G.; Sterin, S.; Mignani, G.; Tinant, B.; Declercq, J.-P.; Chapon, D.; Marko, I. E. J. Organomet. Chem. 2005, 690, 6156.
110. (c) Jankowiak, M.; Maciejewski, H.; Gulinski, J. J. Organomet. Chem. 2005, 690, 4478.
111. (d) Oyamada, H.; Akiyama, R.; Hagio, H.; Naito, T.; Kobayashi, S. Chem. Commun. 2006, 41, 4297.
112. (e) Poyatos, M.; Maisse-Francois, A.; Bellemin-Lapponaz, S.; Gade, L. H. Organometallics 2006, 25, 2634.
113. (f) Zhao, L.; Loy, D. A.; Shea, K. J. J. Am. Chem. Soc. 2006, 128, 14250.
114. Oshima, K. VII.5 Metallopalladation. In Handbook on Organopalladium Chemistry; Negishi, E., Ed.; Wiley: New York, 2002; p 2825.
115. Pohlmann, T.; de Meijere, A. Org. Lett. 2000, 2, 3877.
116. (a) Sagawa, T.; Sakamoto, Y.; Tanaka, R.; Katayama, H.; Ozawa, F. Organometallics 2003, 22, 4433.
117. (b) Hemeon, I.; Singer, R. D. J. Mol. Catal. A: Chem. 2004, 214, 33.
118. Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754.
119. (a) Mori, M.; Hirose, T.; Wakamatsu, H.; Imakuni, N.; Sato, Y. Organometallics 2001, 20, 1907.
120. (b) Shin, S.; RajanBabu, T. V. J. Am. Chem. Soc. 2001, 123, 8416.
121. (c) Sato, Y.; Imakuni, N.; Hirose, T.; Wakamatsu, H.; Mori, M. J. Organomet. Chem. 2003, 687, 392.
122. (d) Kumareswaran, R.; Shin, S.; Gallou, I.; RajanBabu, T. V. J. Org. Chem. 2004, 69, 7157.
123. Larhed, M.; Hallberg, A. IV.2.1.1 Scope, mechanism, and other fundamental aspects of the intermolecular Heck reaction. In Handbook on Organopalladium Chemistry; Negishi, E., Ed.; Wiley: New York, 2002; p 1133.
124. (a) Baekelmans, P.; Gielen, M.; Nasielski, J. Tetrahedron Lett. 1967, 8, 1149.
125. (b) Gielen, M.; Baekelmans, P.; Nasielski, J. J. Organomet. Chem. 1972, 34, 329.
126. See Supporting Information for details.