Highly enantioselective [3+2] annulation of cyclic enol silyl ethers with donor-acceptor cyclopropanes: Accessing 3a-hydroxy [n.3.0]carbobicycles

Angewandte Chemie - International Edition

Volumn 52, Issue 14, 2013, Pages 4004-4007

  Xu, Hao ^a   Qu, Jian Ping ^a   Liao, Saihu ^a   Xiong, Hu ^a   Tang, Yong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

annulations; asymmetric catalysis; copper; fused ring systems; small rings

Indexed keywords

ANNULATIONS; ASYMMETRIC CATALYSIS; DONOR-ACCEPTOR CYCLOPROPANES; ENANTIOSELECTIVE; ENOL SILYL ETHERS; FUSED-RING SYSTEM; NATURAL PRODUCTS; SMALL RINGS;

BENZENE REFINING; COPPER;

ETHERS;

BICYCLO COMPOUND; CARBON; COPPER; CYCLOPROPANE DERIVATIVE; ETHER DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLOADDITION; STEREOISOMERISM;

BICYCLO COMPOUNDS; CARBON; CATALYSIS; COPPER; CYCLOADDITION REACTION; CYCLOPROPANES; ETHERS; STEREOISOMERISM;

EID: 84875759358     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201300032     Document Type: Article

References (91)

1. J. L. Reino, R. Durán-Patrón, I. Segura, R. Hernández-Galán, H. H. Riese, I. G. Collado, J. Nat. Prod. 2003, 66, 344
2. A. del C. Coronel, C. M. Cerda-García-Rojas, P. Joseph-Nathan, C. A. N. Catalán, Flavour Fragrance J. 2006, 21, 839
3. M. A. C. Kaplan, H. R. L. Pugialli, D. Lopes, H. E. Cottlieb, Phytochemistry 2000, 55, 749
4. L. Villaescusa Castillo, A. M. D. Lanza, R. Faure, L. Debrauwer, R. Elias, G. Guybalansard, Phytochemistry 1995, 40, 1193
5. R. Battaglia, M. D. Bernardi, G. Fornza, G. Mellerio, G. Vidari, P. V. Finsi, J. Nat. Prod. 1980, 43, 319
6. J.-H. Yang, J.-X. Pu, J. Wen, X.-N. Li, F. He, Y.-B. Xue, Y.-Y. Wang, Y. Li, W.-L. Xiao, H.-D. Sun, J. Nat. Prod. 2010, 73, 12
7. S. Liang, Y.-H. Shen, Y. Feng, J.-M. Tian, X.-H. Liu, Z. Xiong, W.-D. Zhang, J. Nat. Prod. 2010, 73, 532
8. X. Wu, S. Lin, C. Zhu, Z. Yue, Y. Yu, F. Zhao, B. Liu, J. Dai, J. Shi, J. Nat. Prod. 2010, 73, 1294.
9. A. G. Angoh, D. L. J. Clive, J. Chem. Soc. Chem. Commun. 1985, 941
10. K. Miura, K. Fugami, K. Oshima, K. Utimoto, Tetrahedron Lett. 1988, 29, 5135
11. M. Nagai, J. Lazor, C. S. Wilcox, J. Org. Chem. 1990, 55, 3440
12. V. H. Rawal, R. C. Newton, V. Krishnamurthy, J. Org. Chem. 1990, 55, 5181
13. S. Kim, S. Lee, J. S. Koh, J. Am. Chem. Soc. 1991, 113, 5106
14. S. Kim, J. S. Koh, J. Chem. Soc. Chem. Commun. 1992, 1377
15. G. A. Molander, J. A. McKie, J. Org. Chem. 1994, 59, 3186
16. G. A. Molander, S. R. Shakya, J. Org. Chem. 1996, 61, 5885
17. S. Tsunoi, I. Ryu, S. Yamasaki, M. Tanaka, N. Sonoda, M. Komatsu, Chem. Commun. 1997, 1889
18. G. A. Molander, C. N. Wolfe, J. Org. Chem. 1998, 63, 9031
19. K. Kakiuchi, Y. Fujioka, H. Yamamura, K. Tsutsumi, T. Morimoto, H. Kurosawa, Tetrahedron Lett. 2001, 42, 7595
20. D. Parmar, H. Matsubara, K. Price, M. Spain, D. J. Procter, J. Am. Chem. Soc. 2012, 134, 12751.
21. G. S. Weatherhead, G. A. Cortez, R. R. Schrock, A. H. Hoveyda, Proc. Natl. Acad. Sci. USA 2004, 101, 5805
22. M. S. Dowling, C. D. Vanderwal, J. Org. Chem. 2010, 75, 6908
23. C. Aouf, N. Galy, H. Doucet, M. Santelli, Appl. Organomet. Chem. 2010, 24, 794
24. G. Mehta, S. Yaragorla, Tetrahedron Lett. 2011, 52, 4485
25. F. Gao, C. T. M. Stamp, P. D. Thornton, T. S. Cameron, L. E. Doyle, D. O. Miller, D. J. Burnell, Chem. Commun. 2012, 48, 233.
26. R. D. Clark, K. G. Untch, J. Org. Chem. 1979, 44, 248
27. W. T. Brady, R. M. Lloyd, J. Org. Chem. 1979, 44, 2560
28. C. S. Pak, S. K. Kim, J. Org. Chem. 1990, 55, 1954
29. W. A. Loughlin, M. A. McCleary, Org. Biomol. Chem. 2003, 1, 1347
30. K. Takasu, M. Ueno, K. Inanaga, M. Ihara, J. Org. Chem. 2004, 69, 517
31. K. Takasu, S. Nagao, M. Ueno, M. Ihara, Tetrahedron 2004, 60, 2071
32. K. Inanaga, K. Takasu, M. Ihara, J. Am. Chem. Soc. 2005, 127, 3668; and catalytic asymmetric variants
33. E. Canales, E. J. Corey, J. Am. Chem. Soc. 2007, 129, 12686
34. K. Ishihara, M. Fushimi, J. Am. Chem. Soc. 2008, 130, 7532; [3+2] Annulations
35. Y. Takahashi, K. Tanino, I. Kuwajima, Tetrahedron Lett. 1996, 37, 5943
36. K. Masuya, K. Domon, K. Tanino, I. Kuwajima, J. Am. Chem. Soc. 1998, 120, 1724.
37. K. Saigo, S. Shimada, T. Shibasaki, M. Hasegawa, Chem. Lett. 1990, 1093
38. M. Komatsu, I. Suehiro, Y. Horiguchi, I. Kuwajima, Synlett 1991, 771
39. Y. Horiguchi, I. Suehiro, A. Sasaki, I. Kuwajima, Tetrahedron Lett. 1993, 34, 6077
40. K. Takasu, S. Nagao, M. Ihara, Adv. Synth. Catal. 2006, 348, 2376
41. J. Fang, J. Ren, Z. Wang, Tetrahedron Lett. 2008, 49, 6659
42. F. de Nanteuil, J. Waser, Angew. Chem. 2011, 123, 12281
43. Angew. Chem. Int. Ed. 2011, 50, 12075.
44. J.-P. Qu, C. Deng, J. Zhou, X.-L. Sun, Y. Tang, J. Org. Chem. 2009, 74, 7684
45. J.-P. Qu, Y. Liang, H. Xu, X.-L. Sun, Z.-X. Yu, Y. Tang, Chem. Eur. J. 2012, 18, 2196.
46. D. Schinzer, M. Ruppelt, Chem. Ber. 1991, 124, 247
47. T. Shono, N. Kise, T. Fujimoto, N. Tominaga, H. Morita, J. Org. Chem. 1992, 57, 7175
48. S. Janardhanam, K. Rajagopalan, J. Chem. Soc. Perkin Trans. 1 1992, 2727
49. H. Maeda, T. Maki, H. Ashie, H. Ohmori, J. Chem. Soc. Chem. Commun. 1995, 871
50. A. Klein, M. Miesch, Tetrahedron Lett. 2003, 44, 4483
51. N. D. Litvinas, B. H. Brodsky, J. D. Bois, Angew. Chem. 2009, 121, 4583
52. Angew. Chem. Int. Ed. 2009, 48, 4513
53. T. Liu, X. Zhao, L. Lu, T. Cohen, Org. Lett. 2009, 11, 4576
54. N. Saito, Y. Sugimura, Y. Sato, Org. Lett. 2010, 12, 3494
55. C. Schäfer, M. Miesch, L. Miesch, Org. Biomol. Chem. 2012, 10, 3253.
56. G. Desimoni, G. Faita, P. Quadrelli, Chem. Rev. 2003, 103, 3119
57. S. Kanemasa, K. Ito, Eur. J. Org. Chem. 2004, 4741
58. P. K. Singh, V. K. Singh, Pure Appl. Chem. 2012, 84, 1651.
59. M. P. Sibi, Z. Ma, C. P. Jasperse, J. Am. Chem. Soc. 2005, 127, 5764
60. Y.-B. Kang, X.-L. Sun, Y. Tang, Angew. Chem. 2007, 119, 3992
61. Angew. Chem. Int. Ed. 2007, 46, 3918
62. A. T. Parsons, J. S. Johnson, J. Am. Chem. Soc. 2009, 131, 3122
63. A. T. Parsons, A. G. Smith, A. J. Neel, J. S. Johnson, J. Am. Chem. Soc. 2010, 132, 9688
64. B. M. Trost, P. J. Morris, Angew. Chem. 2011, 123, 6291
65. Angew. Chem. Int. Ed. 2011, 50, 6167
66. Y.-Y. Zhou, J. Li, L. Ling, S.-H. Liao, X.-L. Sun, Y.-X. Li, L.-J. Wang, Y. Tang, Angew. Chem. 2013, 125, 1492
67. Angew. Chem. Int. Ed. 2013, 52, 1452; For general reviews on D-A cyclopropanes, see
68. H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151
69. C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009, 38, 3051
70. P. Tang, Y. Qin, Synthesis 2012, 2969.
71. J. Zhou, Y. Tang, Chem. Soc. Rev. 2005, 34, 664
72. L. H. Gade, S. Bellemin-Laponnaz, Chem. Eur. J. 2008, 14, 4142
73. G. C. Hargaden, P. J. Guiry, Chem. Rev. 2009, 109, 2505. For selected examples, see
74. J. Zhou, Y. Tang, J. Am. Chem. Soc. 2002, 124, 9030
75. R. Rasappan, M. Hager, A. Gissibl, O. Reiser, Org. Lett. 2006, 8, 6099
76. M. Seitz, C. Capacchione, S. Bellemin-Laponnaz, H. Wadepohl, B. D. Ward, L. H. Gade, Dalton Trans. 2006, 193
77. C. Foltz, M. Enders, S. Bellemin-Laponnaz, H. Wadepohl, L. H. Gade, Chem. Eur. J. 2007, 13, 5994
78. C. Foltz, B. Stecker, G. Marconi, S. Bellemin-Laponnaz, H. Wadepohl, L. H. Gade, Chem. Eur. J. 2007, 13, 9912
79. A. Schätz, R. Rasappan, M. Hager, A. Gissibl, O. Reiser, Chem. Eur. J. 2008, 14, 7259
80. R. Rasappan, T. Olbrich, O. Reiser, Adv. Synth. Catal. 2009, 351, 1961
81. M. Hager, S. Wittmann, A. Schätz, F. Pein, P. Kreitmeier, O. Reiser, Tetrahedron: Asymmetry 2010, 21, 1194.
82. V. L. Rendina, D. C. Moebius, J. S. Kingsbury, Org. Lett. 2011, 13, 2004
83. M. R. Castillo, S. Castillón, C. Claver, J. M. Fraile, A. Gual, M. Martín, J. A. Mayoral, E. Sola, Tetrahedron 2011, 67, 5402
84. T. Sawada, M. Nakada, Tetrahedron: Asymmetry 2012, 23, 350
85. V. L. Rendina, H. Z. Kaplan, J. S. Kingsbury, Synthesis 2012, 686
86. Y.-Y. Zhou, L.-J. Wang, J. Li, X.-L. Sun, Y. Tang, J. Am. Chem. Soc. 2012, 134, 9066
87. J. Li, S.-H. Liao, H. Xiong, Y.-Y. Zhou, X.-L. Sun, Y. Zhang, X.-G. Zhou, Y. Tang, Angew. Chem. 2012, 124, 8968
88. Angew. Chem. Int. Ed. 2012, 51, 8838
89. C. Deng, L.-J. Wang, J. Zhu, Y. Tang, Angew. Chem. 2012, 124, 11788
90. Angew. Chem. Int. Ed. 2012, 51, 11620.
91. CCDC 917548 (3 aa -cis), 917502 (3 da -trans), and 917503 (3 gc) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.