Rhodium-catalyzed regioselective carboacylation of olefins: A C-C bond activation approach for accessing fused-ring systems

Angewandte Chemie - International Edition

Volumn 51, Issue 30, 2012, Pages 7567-7571

  Xu, Tao ^a   Dong, Guangbin ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

annulation; C C activation; carboacylation; fused ring systems; homogeneous catalysis

Indexed keywords

ANNULATION; C-C ACTIVATIONS; CARBOACYLATION; FUSED-RING SYSTEM; HOMOGENEOUS CATALYSIS;

CATALYSIS; REACTION KINETICS; REGIOSELECTIVITY; RHODIUM;

OLEFINS;

EID: 84864271029     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201202771     Document Type: Article

References (101)

1. B. M. Trost, Science 1991, 254, 1471.
2. A. Padwa, Tetrahedron 2011, 67, 8057
3. U. Chiacchio, A. Padwa, G. Romeo, Curr. Org. Chem. 2009, 13, 422
4. M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49
5. H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151
6. M. Murakami, Angew. Chem. 2003, 115, 742
7. Angew. Chem. Int. Ed. 2003, 42, 718
8. S. E. Gibson, N. Mainolfi, Angew. Chem. 2005, 117, 3082
9. Angew. Chem. Int. Ed. 2005, 44, 3022
10. M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117
11. Z.-X. Yu, Y. Wang, Chem. Asian J. 2010, 5, 1072
12. P.-A. Inglesby, P. A. Evans, Chem. Soc. Rev. 2010, 39, 2791
13. G. Jiang, Y. Wang, Z.-X. Yu, in Science of Synthesis: Stereoselective Synthesis, Vol. 3 (Ed.:, P. A. Evans,), Thieme, Stuttgart, 2011, p. 7
14. F. Lõpez, J. L. Mascareñas, Chem. Eur. J. 2011, 17, 418
15. P. A. Wender, G. Gamber, T. J. Williams, in Modern Rhodium-Catalyzed Organic Reactions (Ed.:, P. A. Evans,), Wiley-VCH, Weinheim, 2005, p. 263
16. B. M. Trost, Angew. Chem. 1986, 98, 1.
17. B. Rybtchinski, D. Milstein, Angew. Chem. 1999, 111, 918
18. Angew. Chem. Int. Ed. 1999, 38, 870
19. M. Murakami, Y. Ito, Top. Organomet. Chem. 1999, 3, 97
20. M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759
21. C.-H. Jun, Chem. Soc. Rev. 2004, 33, 610
22. T. Satoh, M. Miura, Top. Organomet. Chem. 2005, 14, 1
23. C.-H. Jun, J.-W. Park, Top. Organomet. Chem. 2007, 24, 117
24. D. Necas, M. Kotora, Curr. Org. Chem. 2007, 11, 1566
25. R. H. Crabtree, Chem. Rev. 1985, 85, 245
26. W. D. Jones, Nature 1993, 364, 676.
27. F. De Simone, J. Waser, Synthesis 2009, 3353
28. M. Yu, B. L. Pagenkopf, Tetrahedron 2005, 61, 321
29. M. J. Campbell, J. S. Johnson, A. T. Parsons, P. D. Pohlhaus, S. D. Sanders, J. Org. Chem. 2010, 75, 6317
30. P. Binger, H. M. BÅch, Top. Curr. Chem. 1987, 135, 77
31. A. Brandi, A. Goti, Chem. Rev. 1998, 98, 589
32. A. Brandi, S. Cicchi, F. M. Cordero, A. Goti, Chem. Rev. 2003, 103, 1213
33. M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117; see Refs. [2d] and [2g].
34. For a recent review, see:, H. Nemoto, Chem. Pharm. Bull. 2007, 55, 961; for a book series, see: Small Ring Compounds in Organic Synthesis I-III (Ed: A. de Meijere), Springer, Berlin, 1986, 1987 and 1988.
35. D. Bellus, B. Ernst, Angew. Chem. 1988, 100, 820
36. Angew. Chem. Int. Ed. Engl. 1988, 27, 797
37. T. Seiser, T. Saget, D. N. Tran, N. Cramer, Angew. Chem. 2011, 123, 7884
38. Angew. Chem. Int. Ed. 2011, 50, 7740.
39. N. Cramer, T. Seiser, Synlett 2011, 449.
40. For a catalytic C-C bond activation reaction of biphenylene, see:, B. L. Edelbach, R. J. Lachicotte, W. D. Jones, J. Am. Chem. Soc. 1998, 120, 2843.
41. C.-H. Jun, C. W. Moon, D.-Y. Lee, Chem. Eur. J. 2002, 8, 2423
42. Y. J. Park, J.-W. Park, C.-H. Jun, Acc. Chem. Res. 2008, 41, 222.
43. J. W. Suggs, C.-H. Jun, J. Am. Chem. Soc. 1986, 108, 4679
44. J. W. Suggs, C.-H. Jun, J. Am. Chem. Soc. 1984, 106, 3054
45. A. M. Dreis, C. J. Douglas, J. Am. Chem. Soc. 2009, 131, 412
46. M. T. Wentzel, V. J. Reddy, T. K. Hyster, C. J. Douglas, Angew. Chem. 2009, 121, 6237
47. Angew. Chem. Int. Ed. 2009, 48, 6121
48. H. Li, Y. Li, X.-S. Zhang, K. Chen, X. Wang, Z.-J. Shi, J. Am. Chem. Soc. 2011, 133, 15244
49. Z.-Q. Lei, H. Li, Y. Li, X.-S. Zhang, K. Chen, X. Wang, Z.-J. Shi, Angew. Chem. 2012, 124, 2744
50. Angew. Chem. Int. Ed. 2012, 51, 2690
51. K. Chen, K. H. Li, Y. Li, X.-S. Zhang, Z.-Q. Lei, Z.-J. Shi, Chem. Sci. 2012, 3, 1634.
52. R. L. Danheiser, S. K. Gee, J. Org. Chem. 1984, 49, 1672
53. R. L. Danheiser, A. Nishida, S. Savariar, M. P. Trova, Tetrahedron Lett. 1988, 29, 4917.
54. P. Schiess, M. Eberle, M. Huys-Francotte, J. Wirz, Tetrahedron Lett. 1984, 25, 2201.
55. L. S. Liebeskind, S. L. Baysdon, Tetrahedron Lett. 1984, 25, 1747
56. L. S. Liebeskind, L. P. Leeds, S. L. Baysdon, J. Am. Chem. Soc. 1984, 106, 6451
57. M. A. Huffman, L. S. Liebeskind, W. T. Pennington, Organometallics 1990, 9, 2194
58. M. A. Huffman, L. S. Liebeskind, W. T. Pennington, Organometallics 1992, 11, 255
59. M. A. Huffman, L. S. Liebeskind, J. Am. Chem. Soc. 1990, 112, 8617
60. M. A. Huffman, L. S. Liebeskind, J. Am. Chem. Soc. 1991, 113, 2771.
61. L. S. Liebeskind, M. S. South, J. Am. Chem. Soc. 1984, 106, 4181.
62. T. Kondo, Y. Taguchi, Y. Kaneko, M. Niimi, T. Mitsudo, Angew. Chem. 2004, 116, 5483
63. Angew. Chem. Int. Ed. 2004, 43, 5369
64. T. Kondo, M. Niimi, M. Nomura, K. Wada, T. Mitsudo, Tetrahedron Lett. 2007, 48, 2837; For recent reviews, see
65. T. Kondo, Synlett 2008, 629
66. T. Kondo, T. Mitsudo, Chem. Lett. 2005, 34, 1462.
67. A-;L. Auvinet, J. P. A. Harrity, Angew. Chem. 2011, 123, 2821
68. Angew. Chem. Int. Ed. 2011, 50, 2769.
69. M. Murakami, M. Makino, S. Ashida, T. Matsuda, Bull. Chem. Soc. Jpn. 2006, 79, 1315, and ref. [3b]
70. M. Murakami, H. Amii, Y. Ito, Nature 1994, 370, 540
71. M. Murakami, H. Amii, K. Shigeto, Y. Ito, J. Am. Chem. Soc. 1996, 118, 8285.
72. M. Murakami, T. Itahashi, Y. Ito, J. Am. Chem. Soc. 2002, 124, 13976.
73. The use of a vinyl cyclobutanone in a [6+2] cycloaddition as an efficient strategy for accessing eight-membered rings was first developed by Wender, see:, P. A. Wender, A. G. Correa, Y. Sato, R. Sun, J. Am. Chem. Soc. 2000, 122, 7815.
74. M. Murakami, S. Ashida, T. Matsuda, J. Am. Chem. Soc. 2005, 127, 6932
75. M. Murakami, N. Ishida, T. Miura, Chem. Commun. 2006, 643
76. L. Liu, N. Ishida, M. Murakami, Angew. Chem. 2012, 124, 2535
77. Angew. Chem. Int. Ed. 2012, 51, 2485.
78. For a review on the synthesis of morphine and related alkaloids, see:, N. Chida, Top. Curr. Chem. 2011, 299, 1, and references therein; for the isolation and related biological studies of parviflorene J, see
79. M. Tamaki, S. K. Sadhu, T. Ohtsuki, K. Toume, T. Koyano, T. Kowithayakorn, M. Hayashi, K. Komiyama, M. Ishibashi, Heterocycles 2007, 72, 649; for the isolation and related biological studies of carnosic acid 12-methyl ether Î-lactone and cycloinumakiol, see
80. Z. Djarmati, R. M. Jankov, A. Djordjevic, B. Ribar, D. Lazar, P. Engel, Phytochemistry 1992, 31, 1307
81. J. G. Urones, S. S. Marcos, D. Diez, R. L. Cubilla, Phytochemistry 1998, 48, 1035
82. M. W. Pertino, C. Theoduloz, J. A. Rodriguez, T. Yanez, V. Lazo, G. Schmeda-Hirschmann, J. Nat. Prod. 2010, 73, 639
83. K. P. Devkota, et al., J. Nat. Prod. 2011, 74, 374.
84. J. P. Lutz, C. M. Rathbun, S. M. Stevenson, B. M. Powell, T. S. Boman, C. E. Baxter, J. M. Zona, J. B. Johnson, J. Am. Chem. Soc. 2012, 134, 715; see also Refs. [10c], [10d], [18], and [20].
85. P. A. Wender, T. E. Jenkins, S. Suzuki, J. Am. Chem. Soc. 1995, 117, 1843
86. D. J. R. O'Mahony, D. B. Belanger, T. Livinghouse, Org. Biomol. Chem. 2003, 1, 2038
87. K. Aikawa, S. Akutagawa, K. Mikami, J. Am. Chem. Soc. 2006, 128, 12648
88. D. Shu, X. Li, M. Zhang, P. J. Robichaux, W. Tang, Angew. Chem. 2011, 123, 1382
89. Angew. Chem. Int. Ed. 2011, 50, 1346
90. G.-J. Jiang, X.-F. Fu, Q. Li, Z.-X. Yu, Org. Lett. 2012, 14, 692
91. S. I. Lee, J. H. Park, Y. K. Chung, S.-G. Lee, J. Am. Chem. Soc. 2004, 126, 2714
92. L. Jiao, M. Lin, L.-G. Zhuo, Z.-X. Yu, Org. Lett. 2010, 12, 2528
93. C. Li, H. Zhang, J. Feng, Y. Zhang, J. Wang, Org. Lett. 2010, 12, 3082.
94. P. J. Dierkes, J. Chem. Soc. Dalton Trans. 1999, 1519.
95. For a kinetic study on the effect of bite angle on reductive elimination, see:, J. E. Marcone, K. G. Moloy, J. Am. Chem. Soc. 1998, 120, 8527.
96. For a single example of a carbocyanation of acyclic trisubstituted olefins, see:, Y. Nakao, S. Ebata, A. Yada, T. Hiyama, M. Ikawa, S. Ogoshi, J. Am. Chem. Soc. 2008, 130, 12874.
97. For the use of Lewis acids in promoting alkene carbocyanation, see:, M. P. Watson, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 12594, Ref. [31], and references therein.
98. For examples of Lewis acid promoted C-C bond cleavage, see:, M. Turska, D. Nečas, P. Drabina, M. Sedlák, M. Kotora, Organometallics 2006, 25, 901, and Ref. [13d].
99. Q. Shen, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 7734
100. T. Yamamoto, M. Abla, Y. Murakami, Bull. Chem. Soc. Jpn. 2002, 75, 1997
101. J. Huang, C. M. Haar, S. P. Nolan, Organometallics 1999, 18, 297.