Allenes as three-carbon units in catalytic cycloadditions: New opportunities with transition-metal catalysts

Chemistry - A European Journal

Volumn 17, Issue 2, 2011, Pages 418-428

  Lõpez, Fernando ^a   Mascareñas, José Luis ^b  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

allenes; cycloaddition; gold; homogeneous catalysis; synthetic methods

Indexed keywords

ALLENES; CYCLOADDITION REACTION; CYCLOADDITIONS; HOMOGENEOUS CATALYSIS; NEW OPPORTUNITIES; SYNTHETIC METHODS; TRANSITION METAL CATALYSTS;

CATALYSIS; CATALYSTS; HYDROCARBONS; PLATINUM; REACTION KINETICS; TRANSITION METALS;

CYCLOADDITION;

EID: 78651252323     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002366     Document Type: Article

References (132)

1. S. Ma, Acc. Chem. Res. 2009, 42, 1679-1688
2. H. Kim, L. J. Williams, Curr. Opin. Clin. Drug Discovery Dev. 2008, 11, 870-894
3. H. Hassan, Curr. Org. Chem. 2007, 11, 413-439
4. S. Ma, Aldrichimica Acta 2007, 40, 91-102
5. S. Ma, Chem. Rev. 2005, 105, 2829-2871
6. L. K. Sydnes, Chem. Rev. 2003, 103, 1133-1150
7. R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067-3126
8. R. W. Bates, V. Satcharoen, Chem. Soc. Rev. 2002, 31, 12-21
9. Modern Allene Chemistr y (Eds.:, N. Krause, A. S. K. Hashmi,), Wiley-VCH, Weinheim, 2004
10. Cumulenes and Allenes in Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, Vol 44 (Ed.:, N. Krause,), Thieme, Stuttgart, 2008.
11. W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990
12. B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Soc. Rev. 2010, 39, 783-816.
13. For selected recent examples, see: (2+2)
14. N. Saito, Y. Tanaka, Y. Sato, Org. Lett. 2009, 11, 4124-4126
15. see also reference [2b]; (2+2+1)
16. P. A. Wender, M. P. Croatt, N. M. Deschamps, Angew. Chem. 2006, 118, 2519-2522
17. Angew. Chem. Int. Ed. 2006, 45, 2459-2462
18. F. Inagaki, S. Narita, T. Hasegawa, S. Kitagaki, C. Mukai, Angew. Chem. 2009, 121, 2041-2045
19. Angew. Chem. Int. Ed. 2009, 48, 2007-2011; (3+2)
20. H.-T. Chang, T. T. Jayanth, C.-H. Cheng, J. Am. Chem. Soc. 2007, 129, 4166-4167
21. J. Yu, L. He, X.-H. Chen, J. Song, W.-J. Chen, L.-Z. Gong, Org. Lett. 2009, 11, 4946-4949
22. B. Trillo, M. Gulías, F. Lõpez, L. Castedo, J. L. Mascareñas, Adv. Synth. Catal. 2006, 348, 2381-2384; (5+2)
23. Z. X. Yu, P. H. Y. Cheong, P. Liu, C. Y. Legault, P. A. Wender, K. N. Houk, J. Am. Chem. Soc. 2008, 130, 2378-2379; (6+2)
24. J. H. Rigby, S. B. Laurent, Z. Kamal, M. J. Heeg, Org. Lett. 2008, 10, 5609-5612; (5+2+1)
25. H. A. Wegner, A. de Meijere, P. A. Wender, J. Am. Chem. Soc. 2005, 127, 6530-6531; (2+2+2)
26. M. Shanmugasundaram, M. S. Wu, M. Jeganmohan, C. W. Huang, C. H. Cheng, J. Org. Chem. 2002, 67, 7724-7729; (5+1)
27. M. Murakami, K. Itami, M. Ubukata, I. Tsuji, Y. Ito, J. Org. Chem. 1998, 63, 4-5.
28. R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604-1606.
29. R. L. Danheiser, C. A. Kwasigroch, Y.-M. Tsai, J. Am. Chem. Soc. 1985, 107, 7233-7235
30. R. L. Danheiser, E. J. Stoner, H. Koyama, D. S. Yamashita, C. A. Klade, J. Am. Chem. Soc. 1989, 111, 4407-4413.
31. D. A. Evans, Z. K. Sweeney, T. Rovis, J. S. Tedrow, J. Am. Chem. Soc. 2001, 123, 12095-12096.
32. K. Daidouji, K. Fuchibe, T. Akiyama, Org. Lett. 2005, 7, 1051-1053
33. K. Fuchibe, R. Hatemata, T. Akiyama, Tetrahedron Lett. 2005, 46, 8563-8566
34. The mechanism proposed for the allenylstannane cycloadditions (ref. [7b]) slightly differs from that previously established by Danheiser.
35. R. A. Brawn, J. S. Panek, Org. Lett. 2009, 11, 473-476; see also
36. M. J. Curtis-Long, Y. Aye, Chem. Eur. J. 2009, 15, 5402-5416.
37. A. Marinetti, A. Voituriez, Synlett 2010, 174-194
38. Y. Wei, M. Shi, Acc. Chem. Res. 2010, 43, 1005-1018
39. B. J. Cowen, S. J. Miller, Chem. Soc. Rev. 2009, 38, 3102-3116
40. L.-W. Ye, J. Zhou, Y. Tang, Chem. Soc. Rev. 2008, 37, 1140-1152
41. J. L. Methot, W. R. Roush, Adv. Synth. Catal. 2004, 346, 1035-1050.
42. C. Zhang, X. Lu, J. Org. Chem. 1995, 60, 2906-2908
43. Y. Du, X. Lu, Y. Yu, J. Org. Chem. 2002, 67, 8901-8905
44. X. Lu, Z. Lu, X. Zhang, Tetrahedron 2006, 62, 457-460.
45. Y. Xia, Y. Liang, Y. Chen, M. Wang, L. Jiao, F. Huang, S. Liu, Y. Li, Z.-X. Yu, J. Am. Chem. Soc. 2007, 129, 3470-3471
46. Y. Liang, S. Liu, Y. Z. Xia, Y. H. Li, Z.-X. Yu, Chem. Eur. J. 2008, 14, 4361-4373
47. E. Mercier, B. Fonovic, C. Henry, O. Kwon, T. Dudding, Tetrahedron Lett. 2007, 48, 3617-3620.
48. Y. Du, X. Lu, J. Org. Chem. 2003, 68, 6463-6465
49. A. T. Ung, K. Schafer, K. B. Lindsay, S. G. Pyne, K. Amornraksa, R. Wouters, I. Van der Linden, I. Biesmans, A. S. J. Lesage, B. W. Skelton, A. H. White, J. Org. Chem. 2002, 67, 227-233
50. S. G. Pyne, K. Schafer, B. W. Skelton, A. H. White, Chem. Commun. 1997, 2267-2268
51. R. A. Jones, M. J. Krische, Org. Lett. 2009, 11, 1849-1851
52. C. E. Henry, O. Kwon, Org. Lett. 2007, 9, 3069-3072.
53. G. Zhu, Z. Chen, Q. Jiang, D. Xiao, P. Cao, X. Zhang, J. Am. Chem. Soc. 1997, 119, 3836-3837.
54. J. E. Wilson, G. C. Fu, Angew. Chem. 2006, 118, 1454-1457
55. Angew. Chem. Int. Ed. 2006, 45, 1426-1429.
56. A. Voituriez, A. Panossian, N. Fleury-Brégeot, P. Retailleau, A. Marinetti, J. Am. Chem. Soc. 2008, 130, 14030-14031
57. A. Voituriez, A. Panossian, N. Fleury-Brégeot, P. Retailleau, A. Marinetti, Adv. Synth. Catal. 2009, 351, 1968-1976
58. N. Pinto, M. Neel, A. Panossian, P. Retailleau, G. Frison, A. Voituriez, A. Marinetti, Chem. Eur. J. 2010, 16, 1033-1045.
59. B. J. Cowen, S. J. Miller, J. Am. Chem. Soc. 2007, 129, 10988-10989
60. for a related work using DIOP (DIOP=4,5-bis(diphenylphosphinomethyl)-2,2- dimethyl-1,3-dioxolane) as catalyst, see:, D. J. Wallace, R. L. Sidda, R. A. Reamer, J. Org. Chem. 2007, 72, 1051-1054.
61. H. Xiao, Z. Chai, C.-W. Zheng, Y.-Q. Yang, W. Liu, J.-K. Zhang, G. Zhao, Angew. Chem. 2010, 122, 4569-4572
62. Angew. Chem. Int. Ed. 2010, 49, 4467-4470.
63. Z. Xu, X. Lu, Tetrahedron Lett. 1997, 38, 3461-3464; see also
64. Z. Xu, X. Lu, J. Org. Chem. 1998, 63, 5031-5041
65. this kind of 1,3-dipoles can also be generated from butynoates.
66. X.-F. Zhu, C. E. Henry, O. Kwon, Tetrahedron 2005, 61, 6276-6282.
67. Y.-Q. Fang, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 5660-5661; See also
68. L. Jean, A. Marinetti, Tetrahedron Lett. 2006, 47, 2141-2145
69. A. Scherer, J. A. Gladysz, Tetrahedron Lett. 2006, 47, 6335-6337.
70. X.-F. Zhu, A.-P. Schaffner, R. C. Li, O. Kwon, Org. Lett. 2005, 7, 2977-2980; see also
71. X.-F. Zhu, C. E. Henry, J. Wang, T. Dudding, O. Kwon, Org. Lett. 2005, 7, 1387-1390
72. S. Xu, L. Zhou, R. Ma, H. Song, Z. He, Chem. Eur. J. 2009, 15, 8698-8702.
73. X.-F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 2003, 125, 4716-4717.
74. The utility of this methodology was demonstrated by the same authors in the synthesis of indole alkaloids alstonerine and macroline, see:, Y. S. Tran, O. Kwon, Org. Lett. 2005, 7, 4289-4291.
75. R. P. Wurz, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 12234-12235.
76. Y. S. Tran, O. Kwon, J. Am. Chem. Soc. 2007, 129, 12632-12633.
77. For a very recent example of (4+n) cycloadditions (n=1, 2) of related α-substituted allenoates, see:, Q. Zhang, L. Yang, X. Tong, J. Am. Chem. Soc. 2010, 132, 2550-2551.
78. M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49-92.
79. For selected reviews, see A. Fürstner, Chem. Soc. Rev. 2009, 38, 3208-3221
80. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351-3378
81. E. Jiménez-NÃñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350
82. H. C. Shen, Tetrahedron 2008, 64, 7847-7870
83. A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519
84. Angew. Chem. Int. Ed. 2007, 46, 3410-3449
85. D. J. Gorin, F. D. Toste, Nature 2007, 446, 395-403.
86. A. Buzas, F. Gagosz, J. Am. Chem. Soc. 2006, 128, 12614-12615.
87. In this communication Gagosz and co-workers isolate the allenyl ester 29 from the reaction mixture. When it was resubmitted to the catalytic conditions the corresponding bicyclic product was obtained in excellent yield, therefore proving the participation of 29 in the catalytic cycle.
88. This and other Au carbene species described throughout the manuscript can also be understood as a Au-stabilized carbocation; for more information, see D. Benitez, N. D. Shapiro, E. Tkatchouk, Y. M. Wang, W. A. Goddard, F. D. Toste, Nat. Chem. 2009, 1, 482-486
89. G. Seidel, R. Mynott, A. Fürstner, Angew. Chem. 2009, 121, 2548-2551
90. Angew. Chem. Int. Ed. 2009, 48, 2510-2513.
91. L. Zhang, J. Am. Chem. Soc. 2005, 127, 16804-16805.
92. G. Zhang, V. J. Catalano, L. Zhang, J. Am. Chem. Soc. 2007, 129, 11358-11359; see also
93. S. Wang, G. Zhang, L. Zhang, Synlett 2010, 692-706.
94. X. Huang, L. Zhang, J. Am. Chem. Soc. 2007, 129, 6398-6399.
95. (I/III) complexes, see Z. Zhang, C. Liu, R. E. Kinder, X. Han, H. Qian, R. A. Widenhoefer, J. Am. Chem. Soc. 2006, 128, 9066-9073
96. C. Liu, R. A. Widenhoefer, Org. Lett. 2007, 9, 1935-1938
97. J. H. Lee, F. D. Toste, Angew. Chem. 2007, 119, 930-932
98. Angew. Chem. Int. Ed. 2007, 46, 912-914
99. H. Funami, H. Kusama, N. Iwasawa, Angew. Chem. 2007, 119, 927-929
100. Angew. Chem. Int. Ed. 2007, 46, 909-911.
101. For selected examples on related (4+3) cycloadditions involving allenes, see
102. J. Huang, R. P. Hsung, J. Am. Chem. Soc. 2005, 127, 50-51
103. H. Xiong, J. Huang, S. K. Ghosh, R. P. Hsung, J. Am. Chem. Soc. 2003, 125, 12694-12695
104. H. Xiong, R. P. Hsung, C. R. Berry, C. Rameshkumar, J. Am. Chem. Soc. 2001, 123, 7174-7175
105. J. E. Antoline, R. P. Hsung, J. Huang, Z. Song, G. Li, Org. Lett. 2007, 9, 1275-1278.
106. For selected reviews on (4+3) cycloadditions between hetero-allyl cations and dienes, see
107. J. H. Rigby, F. C. Pigge, Org. React. 1998, 51, 351-478
108. M. Harmata, Tetrahedron 1997, 53, 6235-6280
109. M. Harmata, Adv. Cycloaddit. 1997, 4, 41-86
110. J. K. Cha, J. Oh, Curr. Org. Chem. 1998, 2, 217-232
111. M. Harmata, Acc. Chem. Res. 2001, 34, 595-605
112. M. Harmata, Adv. Synth. Catal. 2006, 348, 2297-2306
113. H. M. R. Hoffmann, Angew. Chem. 1984, 96, 29-48
114. Angew. Chem. Int. Ed. Engl. 1984, 23, 1-19
115. M. Harmata, Chem. Commun. 2010,; For selected examples, see
116. M. Harmata, C. B. Gamlath, J. Org. Chem. 1988, 53, 6154-6156
117. M. Harmata, V. R. Fletcher, R. J. Claassen II, J. Am. Chem. Soc. 1991, 113, 9861-9862
118. Y. Hu, L. Ou, D. Bai, Tetrahedron Lett. 1999, 40, 545-548
119. G. Prié, N. Prévost, H. Twin, S. A. Fernandes, J. F. Hayes, M. Shipman, Angew. Chem. 2004, 116, 6679-6681
120. Angew. Chem. Int. Ed. 2004, 43, 6517-6519.
121. B. Trillo, F. Lõpez, M. Gulías, L. Castedo, J. L. Mascareñas, Angew. Chem. 2008, 120, 965-968
122. Angew. Chem. Int. Ed. 2008, 47, 951-954.
123. B. Trillo, F. Lõpez, S. Montserrat, G. Ujaque, L. Castedo, A. Lledõs, J. L. Mascareñas, Chem. Eur. J. 2009, 15, 3336-3339.
124. P. Mauleõn, R. M. Zeldin, A. Z. González, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 6348-6349.
125. B. W. Gung, D. T. Craft, L. N. Bailey, K. Kirschbaum, Chem. Eur. J. 2010, 16, 639-644.
126. For an example of this transannular cycloaddition by using an allene instead of the propargyl acetate, see:, B. W. Gung, D. T. Craft, Tetrahedron Lett. 2009, 50, 2685-2687.
127. I. Alonso, B. Trillo, F. Lõpez, S. Montserrat, G. Ujaque, L. Castedo, A. Lledõs, J. L. Mascareñas, J. Am. Chem. Soc. 2009, 131, 13020-13030
128. D. Benitez, E. Tkatchouk, A. Z. González, W. A. Goddard, F. D. Toste, Org. Lett. 2009, 11, 4798-4801.
129. M. R. Luzung, P. Mauleõn, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 12402-12403.
130. M. Alcarazo, T. Stork, A. Anoop, W. Thiel, A. Fürstner, Angew. Chem. 2010, 122, 2596-2600
131. Angew. Chem. Int. Ed. 2010, 49, 2542-2546.
132. H. Kusama, M. Ebisawa, H. Funami, N. Iwasawa, J. Am. Chem. Soc. 2009, 131, 16352-16353.