A Practical and Enantioselective Approach to Tetrahydrocarbazoles by Asymmetric Organocatalysis

ChemCatChem

Volumn 3, Issue 4, 2011, Pages 679-683

  Zhu, Xiao Yu ^a   An, Xiao Lei ^a   Li, Chang Feng ^a   Zhang, Fu Gen ^a   Hua, Qiu Lin ^a   Chen, Jia Rong ^a   Xiao, Wen Jing ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

Alkylation; Asymmetric synthesis; Enantioselectivity; Heterocycles; Organocatalysis

Indexed keywords

EID: 80051804870     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201000379     Document Type: Article

References (117)

1. R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970;
2. Indoles (Ed.: R.J. Sundberg), Academic Press, San Diego, CA, 1996;
3. thed., Thieme, New York, 2001;
4. J. Bonjoch, D. Solé, Chem. Rev. 2000, 100, 3455-3482;
5. D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev. 2003, 103, 893-930;
6. M. Somei, F. Yamada, Nat. Prod. Rep. 2003, 20, 216-242;
7. S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873-2920.
8. M. Hesse, Alkaloids: Nature's Curse or Blessing?, Wiley-VCH, New York, 2002;
9. M. Somei, F. Yamada, Nat. Prod. Rep. 2005, 22, 73-103;
10. J. A. Joule in Science of Synthesis, Vol.10 (Ed.: E.J. Thomas), Thieme, Stuttgart, Germany, 2000, p.361;
11. G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875-2911.
12. For reviews on catalytic asymmetric Friedel-Crafts alkylations, see:
13. M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560-566; Angew. Chem. Int. Ed. 2004, 43, 550-556;
14. M. Bandini, A. Melloni, F. Piccinelli, in Handbooks of C, H Bonds Transformations, Vol.1 (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005, p.150;
15. M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi, Synlett 2005, 1199-1222;
16. T. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108, 2903-2915;
17. S.-L. You, Q. Cai, M. Zeng, Chem. Soc. Rev. 2009, 38, 2190-2201;
18. Catalytic Asymmetric Friedel-Crafts Alkylations (Eds.: M. Bandini, A.Uman i-Ronchi), Wiley-VCH, Weinheim, 2009;
19. M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9697-9701; Angew. Chem. Int. Ed. 2009, 48, 9533-9537.
20. For selected examples, see:
21. T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2006, 8, 1533-1535;
22. I. T. Raheem, P. S. Thiara, E. A. Peterson, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 13404-13405;
23. J. Franzén, A. Fisher, Angew. Chem. 2009, 121, 801-805; Angew. Chem. Int. Ed. 2009, 48, 787-791;
24. M. E. Muratore, C. A. Holloway, A. W. Pilling, R. I. Storer, G. Trevitt, D. J. Dixon, J. Am. Chem. Soc. 2009, 131, 10796-10797;
25. X.-Y. Wu, X.-Y. Dai, L.-L. Nie, H.-H. Fang, J. Chen, Z.-J. Ren, W.-G. Cao, G. Zhao, Chem. Commun. 2010, 46, 2733-2735.
26. For selected examples, see:
27. M. Agnusdei, M. Bandini, A. Melloni, A. Umani-Ronchi, J. Org. Chem. 2003, 68, 7126-7129;
28. M. Bandini, A. Melloni, F. Piccinelli, R. Sinisi, S. Tommasi, A. Umani-Ronchi, J. Am. Chem. Soc. 2006, 128, 1424-1425;
29. X.-Q. Han, R. A. Widenhoefer, Org. Lett. 2006, 8, 3801-3804;
30. H. Huang, P. René, Angew. Chem. 2009, 121, 612-615; Angew. Chem. Int. Ed. 2009, 48, 604-606;
31. Q. Cai, Z.-A. Zhao, S.-L. You, Angew. Chem. 2009, 121, 7564-7567; Angew. Chem. Int. Ed. 2009, 48, 7428-7431.
32. For selected exmples, see:
33. J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc. 2006, 128, 1086-1087;
34. M. J. Wanner, R. N. S. vanderHaas, K. R. deCuba, J. H. vanMaarseveen, H. Hiemstra, Angew. Chem. 2007, 119, 7629-7631; Angew. Chem. Int. Ed. 2007, 46, 7485-7487;
35. D. J. Mergott, S. J. Zuend, E. N. Jacobsen, Org. Lett. 2008, 10, 745-748;
36. N. V. Sewgobind, M. J. Wanner, S. Ingemann, R. vonGelder, J. H. vanMaarseveen, H. Hiemstra, J. Org. Chem. 2008, 73, 6405-6408.
37. For selected examples on non-asymmetric approaches to THCs, see:
38. C.-Y. Chen, D. R. Lieberman, R. D. Larsen, T. R. Verhoeven, P. J. Reider, J. Org. Chem. 1997, 62, 2676-2677;
39. T. Iwama, V. B. Birman, S. A. Kozmin, V. H. Rawal, Org. Lett. 1999, 1, 673-676;
40. M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 116, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528;
41. C. Liu, R. A. Widenhoefer, J. Am. Chem. Soc. 2004, 126, 10250-10251;
42. M. C. Willis, G. N. Brace, I. P. Holmes, Angew. Chem. 2005, 117, 407-410; Angew. Chem. Int. Ed. 2005, 44, 403-406;
43. C. Liu, R. A. Widenhoefer, Chem. Eur. J. 2006, 12, 2371-2382;
44. Z. Zhang, C. Liu, R. E. Kinder, X. Han, H. Qian, R. A. Widenhoefer, J. Am. Chem. Soc. 2006, 128, 9066-9073;
45. C. Liu, C. F. Bender, X. Han, R. A. Widenhoefer, Chem. Commun. 2007, 3607-3618.
46. For catalytic asymmetric approaches to tetrahydrocarbazoles, see:
47. D. A. Evans, K. R. Fandrick, H.-J. Song, J. Am. Chem. Soc. 2005, 127, 8942-8943;
48. C. Liu, R. A. Widenhoefer, Org. Lett. 2007, 9, 1935-1938.
49. M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9697-9701; Angew. Chem. Int. Ed. 2009, 48, 9533-9537;
50. M. Bandini, A. Eichholzer, A. Gualandi, T. Quinto, D. Savoia, ChemCatChem 2010, 2, 661-665; for previous related work of this group, see:
51. M. Bandini, A. Eichholzer, M. Monari, F. Piccinelli, A. Umani-Ronchi, Eur. J. Org. Chem. 2007, 2917-2920;
52. M. Bandini, A. Eichholzer, M. Tragni, A. Umani-Ronchi, Angew. Chem. 2008, 120, 3282-3285; Angew. Chem. Int. Ed. 2008, 47, 3238-3241.
53. For general reviews on organocatalysis, see:
54. A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005;
55. P. I. Dalk, Enantioselective Organocatalysis: Reactions and Experimental Procedures, Vol.1, Wiley-VCH, Weinheim, 2007;
56. X. Yu, W. Wang, Chem. Asian J. 2008, 3, 516-532;
57. S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178-2189;
58. P. Melchiorre, Angew. Chem. 2009, 121, 1386-1389; Angew. Chem. Int. Ed. 2009, 48, 1360-1363.
59. C. Gioia, A. Hauville, L. Bernardi, F. Fini, A. Ricci, Angew. Chem. 2008, 120, 9376-9379; Angew. Chem. Int. Ed. 2008, 47, 9236-9239;
60. S. B. Jones, B. Simmons, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 13606-13607;
61. K. C. Nicolaou, R. Reingruber, D. Sarlah, S. Bräse, J. Am. Chem. Soc. 2009, 131, 2086-2087.
62. X.-F. Wang, J.-R. Chen, Y.-J. Cao, H.-G. Cheng, W.-J. Xiao, Org. Lett. 2010, 12, 1140-1143.
63. C.-F. Li, H. Liu, J. Liao, Y.-J. Cao, X.-P. Liu, W.-J. Xiao, Org. Lett. 2007, 9, 1847-1850;
64. H.-H. Lu, H. Liu, W. Wu, X.-F. Wang, L.-Q. Lu, W.-J. Xiao, Chem. Eur. J. 2009, 15, 2742-2746;
65. C.-B. Chen, X.-F. Wang, Y.-J. Cao, H.-G. Cheng, W.-J. Xiao, J. Org. Chem. 2009, 74, 3532-3535;
66. L.-Q. Lu, Y.-J. Cao, X.-P. Liu, J. An, C.-J. Yao, Z.-H. Ming, W.-J. Xiao, J. Am. Chem. Soc. 2008, 130, 6946-6948;
67. L.-Q. Lu, F. Li, J. An, J.-J. Zhang, X.-L. An, Q.-L. Hua, W.-J. Xiao, Angew. Chem. 2009, 121, 9706-9709; Angew. Chem. Int. Ed. 2009, 48, 9542-9545;
68. L.-Q. Lu, J.-J. Zhang, F. Li, J. An, Q.-L. Hua, J.-R. Chen, W.-J. Xiao, Angew. Chem. 2010, 122, 4597-4600; Angew. Chem. Int. Ed. 2010, 49, 4495-4498;
69. X.-L. An, J.-R. Chen, C.-F. Li, F.-G. Zhang, Y.-Q. Zou, Y.-C. Guo, W.-J. Xiao, Chem. Asian J. 2010, 5, 2258-2265;
70. H.-G. Cheng, C.-B. Chen, F. Tan, N.-J. Chang, J.-R. Chen, W.-J. Xiao, Eur. J. Org. Chem. 2010, 4976-4980;
71. X.-F. Wang, Q.-L. Hua, Y. Cheng, X.-L. An, Q.-Q. Yang, J.-R. Chen, W.-J. Xiao, Angew. Chem. 2010, 122, 8557-8561; Angew. Chem. Int. Ed. 2010, 49, 8379-8383.
72. J.-R. Chen, C.-F. Li, X.-L. An, J.-J. Zhang, X.-Y. Zhu, W.-J. Xiao, Angew. Chem. 2008, 120, 2523-2526; Angew. Chem. Int. Ed. 2008, 47, 2489-2492.
73. For recent reviews on iminium catalysis, see:
74. G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79-87;
75. A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416-5470; for pioneering works, see:
76. K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244;
77. N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370-4371.
78. H. J. Knölker, K. R. Reddy, Chem. Rev. 2002, 102, 4303-4428.
79. T.-L. Choi, A. K. Chatterjee, R. H. Grubbs, Angew. Chem. 2001, 113, 1317-1319; Angew. Chem. Int. Ed. 2001, 40, 1277-1279.
80. For reviews on diaryl prolinol silyl ether, see:
81. C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042-8046; Angew. Chem. Int. Ed. 2006, 45, 7876-7880;
82. A. Mielgo, C. Palomo, Chem. Asian J. 2008, 3, 922-948; For pioneering work, see:
83. M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804-807; Angew. Chem. Int. Ed. 2005, 44, 794-797;
84. M. Marigo, J. Franzén, T. B. Poulsen, W. Zhuang, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 6964-6965.
85. A. F. Littke, G. C. Fu, Angew. Chem. 1999, 111, 2568-2570; Angew. Chem. Int. Ed. 1999, 38, 2411-2413;
86. J. F. Hartwig, Acc. Chem. Res. 1998, 31, 852-860;
87. J.-A. Ma, D. Cahard, Chem. Rev. 2004, 104, 6119-6146.
88. See the Supporting Information for more details.
89. CCDC775380 (for 11) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
90. E. Baltazzi, L. I. Krimen, Chem. Rev. 1963, 63, 511-556;
91. B. A. Trofimov, L. N. Sobenina, A. P. Demenev, A. I. Mikhaleva, Chem. Rev. 2004, 104, 2481-2506;
92. H. Fan, J. Peng, M. T. Hamann, J.-F. Hu, Chem. Rev. 2008, 108, 264-287;
93. J. A. Johnson, N. Li, D. Sames, J. Am. Chem. Soc. 2002, 124, 6900-6903;
94. A. L. Bowie, C. C. Hughes, D. Trauner, Org. Lett. 2005, 7, 5207-5209;
95. P. S. Baran, J. M. Richter, D. W. Lin, Angew. Chem. 2005, 117, 615-618; Angew. Chem. Int. Ed. 2005, 44, 609-612;
96. B. M. Trost, G. Dong, J. Am. Chem. Soc. 2006, 128, 6054-6055;
97. M. D. Clift, R. J. Thomson, J. Am. Chem. Soc. 2009, 131, 14579-14583;
98. A. Fensome, W. R. Adams, A. L. Adams, T. J. Berrodin, J. Cohen, C. Huselton, A. Illenberger, J. C. Kern, V. A. Hudak, M. A. Marella, E. G. Melenski, C. C. McComas, C. A. Mugford, O. D. Slayden, M. Yudt, Z. Zhang, P. Zhang, Y. Zhu, R. C. Winneker, J. E. Wrobel, J. Med. Chem. 2008, 51, 1861-1873.
99. For recent examples with activated alkenes, see:
100. W. Zhuang, N. Gathergood, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2001, 66, 1009-1013;
101. C. Palomo, M. Oiarbide, B. G. Kardak, J. M. Garcia, A. Linden, J. Am. Chem. Soc. 2005, 127, 4154-4155;
102. D. A. Evans, K. R. Fandrick, Org. Lett. 2006, 8, 2249-2252;
103. H. Liu, J. Xu, D.-M. Du, Org. Lett. 2007, 9, 4725-4728;
104. B. M. Trost, C. Müller, J. Am. Chem. Soc. 2008, 130, 2438-2439;
105. M. Zeng, Q. Kang, Q.-L. He, S.-L. You, Adv. Synth. Catal. 2008, 350, 2169-2173;
106. Y.-F. Sheng, G.-Q. Li, Q. Kang, A.-J. Zhang, S.-L. You, Chem. Eur. J. 2009, 15, 3351-3354; with carbonyl compounds, see:
107. T. D. Beeson, A. Mastracchio, J.-B. Hong, K. Ashton, D. W. C. MacMillan, Science 2007, 316, 582-585;
108. J. C. Conrad, J. Kong, B. N. Laforteza, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 11640-11641;
109. J. Nie, G.-W. Zhang, L. Wang, A. Fu, Y. Zheng, J.-A. Ma, Chem. Commun. 2009, 2356-2358;
110. J. Nie, G.-W. Zhang, L. Wang, D.-H. Zheng, Y. Zheng, J.-A. Ma, Eur. J. Org. Chem. 2009, 3145-3149;
111. G. Blay, I. Fernández, A. Monleón, J. R. Pedro, C. Vila, Org. Lett. 2009, 11, 441-444; with imines, see:
112. G. Li, G. B. Rowland, E. B. Rowland, J. C. Antilla, Org. Lett. 2007, 9, 4065-4068;
113. Q. Kang, X.-J. Zheng, S.-L. You, Chem. Eur. J. 2008, 14, 3539-3542.
114. S. W. Youn, S. J. Pastine, D. Sames, Org. Lett. 2004, 6, 581-584;
115. A. B. Smith, III., M. Visnick, J. N. Haseltine, P. A. Sprengeler, Tetrahedron 1986, 42, 2957-2969;
116. D. P. Curran. M. J. Totleben, J. Am. Chem. Soc. 1992, 114, 6050-6058;
117. H. Zhang, Q. Cai, D.-W. Ma, J. Org. Chem. 2005, 70, 5164-5173.