Enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles with enones catalyzed by primary-secondary diamines

Chemistry - A European Journal

Volumn 15, Issue 42, 2009, Pages 11105-11108

  Hong, Liang ^a   Sun, Wangsheng ^a   Liu, Chunxia ^a   Wang, Lei ^a   Wong, Kwokyin ^b   Wang, Rui ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

Conjugate addition; Enantioselectivity; Enones; Friedel crafts reaction; Organocatalysis

Indexed keywords

ALKYL CHAIN; BENZYLIDENEACETONE; CATALYTIC ACTIVITY; COCATALYST; CONJUGATE ADDITION; ENANTIOSELECTIVE; ENONES; FRIEDEL-CRAFTS ALKYLATION; OPTIMAL REACTION CONDITION; ORGANOCATALYSIS; PRIMARY AMINES;

ALKYLATION; AMINATION; AMINO ACIDS; CATALYSIS; CATALYSTS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; FRIEDEL-CRAFTS REACTION; HYDROCARBONS; ORGANIC ACIDS; RATE CONSTANTS; REACTION KINETICS; TOLUENE;

AMINES;

AMINO ACID; DIAMINE; INDOLE DERIVATIVE; KETONE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ALKYLATION; AMINO ACIDS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; DIAMINES; INDOLES; KETONES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 70350495377     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901635     Document Type: Article

References (110)

1. For selected reviews of organocatalysis, see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 226, 5248;
2. Angew. Chem. Int. Ed. 2004, 43, 5138;
3. b) special issue on organocatalysis: Acc.. Chem. Res. 2004, 37, Issue 8;
4. c) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719;
5. d) B. List, J. W. Yang, Science 2006, 313, 1584;
6. e) B. List, Chem. Commun. 2006, 819;
7. f) M. J. Gaunt, C. C. C. Johansson, A. McNally, N. T. Vo, Drug Discov. Today 2007,12, 8;
8. g) special issue on organocatalysis: Chem. Rev. 2007, 107, Issue 12;
9. h) P. I. Dalko, Enantioselective Organocatalysis, Wiley-VCH, Weinheim, 2007;
10. i) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716;
11. Angew. Chem. Int. Ed. 2008, 47, 4638.
12. a) M. Yamaguchi, T. Shiraishi, M. Hirama, J. Org. Chem. 1996, 61, 3520;
13. b) S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975;
14. c) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458;
15. d) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685;
16. Angew. Chem. Int. Ed. 2003, 42, 661;
17. e) N. Halland, T. Hansen, K. A. Jørgensen, Angew. Chem. 2003, 115, 5105;
18. Angew. Chem. Int. Ed. 2003, 42, 4955;
19. f) F. Tanaka, R. Thayumanavan, N. Mase, C. F. Barbas III, Tetrahedron Lett. 2004, 45, 325;
20. g) S. Pizzarello, A. L. Weber, Science 2004, 303, 1151;
21. h) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2004, 226, 1292;
22. Angew. Chem. Int. Ed. 2004, 43, 1272;
23. i) A. Córdova, W. Zou, I. Ibrahem, E. Reyes, M. Engqvist, W.-W. Liao, Chem. Commun. 2005, 3586;
24. j) I. Ibrahem, W. Zou, M. Engqvist, Y Xu, A. Córdova, Chem. Eur. J. 2005,11, 7024;
25. k) A. Prieto, N. Halland, K. A. Jørgensen, Org. Lett. 2005, 7, 3897;
26. K. R. Knudsen, C. E. T. Mitchell, S. V. Ley, Chem. Commun. 2006, 66;
27. m) Y. Xu, A. Córdova, Chem. Commun. 2006, 460.
28. D.J. Hupe in New Comprehensive Biochemistry, Vol.6 (Ed.: M.I. Page), Elsevier, Amsterdam, 1984, pp. 271-301.
29. a) J. Liu, Z. Yang, Z. Wang, F. Wang, X. Chen, X. Liu, X. Feng, Z. Su, C. Hu, J. Am. Chem. Soc. 2008, 130, 5654;
30. b) S. Luo, H. Xu, L. Chen, J.-P. Cheng, Org. Lett. 2008, 10, 1775;
31. c) S. Luo, H. Xu, L. Zhang, J. Li, J.-P. Cheng, Org. Lett. 2008,10, 653;
32. d) S. Luo, J. Li, L. Zhang, H. Xu, J.-P. Cheng, Chem. Eur. J. 2008, 14, 1273;
33. e) K. H. Kim, S. Lee, D.-W. Lee, D.-H. Ko, D.-C. Ha, Tetrahedron Lett. 2005, 46, 5991;
34. f) S. S. V. Ramasastry, H. Zhang, F. Tanaka, C.F. Barbas III, J. Am. Chem. Soc. 2007, 129, 288;
35. g) P. Ricci, A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Adv. Synth. Catal. 2008, 350, 49;
36. h) C. M. Reisinger, X. Wang, B. List, Angew. Chem. 2008, 120, 8232;
37. Angew. Chem. Int. Ed. 2008, 47, 8112;
38. i)T.-R. Kang, J.-W. Xie, W. Du, X. Feng, Y.-C. Chen, Org. Biomol. Chem. 2008, 6, 2673;
39. j) B. Tan, Z. Shi, P. J. Chua, G. Zhong, Org. Lett. 2008, 10, 3425;
40. k) S. H. McCooey, S. J. Connon, Org. Lett. 2007, 9, 599;
41. J.-W. Xie, L. Yue, W. Chen, W. Du, J. Zhu, J.-G. Deng, Y.-C. Chen, Org. Lett. 2007, 9, 413;
42. m) T.-Y. Liu, H.-L. Cui, Y Zhang, K. Jiang, W. Du, Z.Q. He, Y.-C. Chen, Org. Lett. 2007, 9, 3671;
43. n) S. Luo, H. Xu, J. Li, L. Zhang, J.-P. Cheng, J. Am. Chem. Soc. 2007, 129, 3074;
44. o) W. Chen, W. Du, Y.-Z. Duan, Y. Wu, S.-Y. Yang, Y.-C. Chen, Angew. Chem. 2007, 119, 7811;
45. Angew. Chem. Int. Ed. 2007, 46, 7667;
46. p) X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2008, 130, 6070;
47. q) R. P. Singh, K. Bartelson, Y. Wang, H. Su, X. Lu, L. Deng, J. Am. Chem. Soc. 2008, 130, 2422;
48. r) J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. 2007, 119, 393;
49. Angew. Chem. Int. Ed. 2007, 46, 389;
50. s) X. Lu, Y. Liu, B. Sun, B. Cindric, L. Deng, J. Am. Chem. Soc. 2008, 130, 8134; for some leading reviews, see:
51. t) L.-W. Xu, Y.-X. Lu, Org. Biomol. Chem. 2008, 6, 2047;
52. u) Y.-C. Chen, Synlett 2008, 1919.
53. Y.-Q. Yang, G. Zhao, Chem. Eur. J. 2008,14, 10888.
54. a) M. E. Kuehne, D. E. Podhorez, T. Mulamba, W. G. Bornmann, J. Org. Chem. 1987, 52, 347;
55. b) R. K. Brown in Heterocyclic Compounds, Vol.25 (Ed.: W.J. Houlihan), Wiley-Interscience, New York, 1972;
56. c) R. J. Sundberg in The Chemistry of Indoles (Ed.: A. T. Blomquist), Academic Press, New York, 1970;
57. d) P. Leon, C. Garbay-Jaureguiberry, M. C. Barsi, J. B. LePecq, B. P. Roques, J. Med. Chem. 1987, 30, 2074;
58. e) C. Hashimoto, H.-P. Husson, Tetrahedron Lett. 1988, 29, 4563;
59. f) M. Laronze, J. Sapi, Tetrahedron Lett. 2002, 43, 7925.
60. a) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172;
61. b) J. Zhou, Y. Tang, J. Am. Chem. Soc. 2002, 124, 9030;
62. c) D. A. Evans, K. A. Scheidt, K. R. Fandrick, H. W. Lam, J. Wu, J. Am. Chem. Soc. 2003, 125, 10780;
63. d) C. Palomo, M. Oiarbide, B. G. Kardak, J. M. García, A. Linden, J. Am. Chem. Soc. 2005,127, 4154;
64. e) D. A. Evans, K. R. Fandrick, H.-J. Song, J. Am. Chem. Soc. 2005, 127, 8942;
65. f) Y.-X. Jia, J.-H. Xie, H.-F. Duan, L.-X. Wang, Q.-L. Zhou, Org. Lett. 2006, 8, 1621;
66. g) S.-F. Lu, D.-M. Du, J. Xu, Org. Lett. 2006, 8, 2115;
67. h) H. Li, Y-Q. Wang, L. Deng, Org. Lett. 2006, 8, 4063;
68. i) W. Zhou, L.-W. Xu, L. Li, L. Yang, C.-G. Xia, Eur. J. Org. Chem. 2006, 5225;
69. j) G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403;
70. k) C.-F. Li, H. Liu, J. Liao, Y.-J. Cao, X.-P. Liu, W.-J. Xiao, Org. Lett. 2007, 9, 1847;
71. H. Yang, Y.-T. Hong, S. Kim, Org. Lett. 2007, 9, 2281;
72. m) G. Blay, I. Fernández, J. R. Pedro, C. Vila, Org. Lett. 2007, 9, 2601;
73. n) H.-M. Dong, H.-H. Lu, L.-Q. Lu, C.-B. Chen; W.-J. Xiao, Adv. Synth. Catal. 2007, 349, 1597;
74. W.-J. Xiao, Adv. Synth. Catal. 2007, 349, 1597;
75. o) M. Rueping, B. J. Nachtsheim, S. A. Moreth, M. Bolte, Angew. Chem. 2008, 120, 603;
76. Angew. Chem. Int. Ed. 2008, 47, 593;
77. p) J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2008, 120, 4080;
78. Angew. Chem. Int. Ed. 2008, 47, 4016;
79. q) H.-Y. Tang, A.-D. Lu, Z.H. Zhou, G.-F. Zhao, L.-N. He, C.-C. Tang, Eur. J. Org. Chem. 2008, 1406.
80. For recent reviews of Friedel-Crafts alkylation reaction, see: a) M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 226, 560;
81. Angew. Chem. Int. Ed. 2004, 43, 550;
82. b) K. A. Jørgensen, Synthesis 2003, 1117;
83. c) Y. Wang, K.-L. Ding, Chin. J. Org. Chem. 2001, 21, 763;
84. d) T. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108, 2903;
85. e) M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi, Synlett 2005, 1199;
86. f) M. Bandini, A. Umani-Ronchi, Catalytic Asymmetric Friedel-Crafts Alkylations, Wiley-VCH, Weinheim, 2009.
87. a) H. Çavdar, N. Saraçoǧlu, Tetrahedron 2005, 62, 2401;
88. b) H. Çavdar, N. Saraçoglu, J. Org. Chem. 2006, 71, 7793;
89. c) D. A. Evans, K. R. Fandrick, Org. Lett. 2006, 8, 2249;
90. d) D. A. Evans, K. R. Fandrick, H.-J. Song, K. A. Scheidt, R. Xu, J. Am. Chem. Soc. 2007,129, 10029;
91. e) G. Blay, I. Fernández, J. R. Pedro, C. Vila, Tetrahedron Lett. 2007, 48, 6731;
92. f) G. Blay, I. Fernández, A. Monleón, J. R. Pedro, C. Vila, Org. Lett. 2009, 11, 441;
93. g) Q. Kang, X.-J. Zheng, S.L. You, Chem. Eur. J. 2008, 14, 3539;
94. h) M. Zeng, Q. Kang, Q.-L. He, S.-L. You, Adv. Synth. Catal. 2008, 350, 2169;
95. i) Y.-F. Sheng, G.Q. Li, Q. Kang, A.-J. Zhang, S.-L. You, Chem. Eur. J. 2009,15, 3351.
96. a) L. Hong, L, Wang, C. Chen, B. Zhang, R. Wang, Adv. Synth. Catal. 2009, 351, 772;
97. b) L. Hong, C. Liu, W. Sun, L. Wang, K. Wong, R. Wang, Org. Lett. 2009,11, 2177.
98. In our initial experiments, the use of diphenylprolinol ether promoted the reaction in poor yield (< 10% yield).
99. a) B. Török, M. Abid, G. London, J. Esquibel, M. Török, S. C. Mhadgut, P. Yan and G. K. S. Prakash, Angew. Chem. 2005, 117, 3146;
100. Angew. Chem. Int. Ed. 2005, 44, 3086;
101. b) H. Li, Y. Q. Wang, L. Deng, Org. Lett. 2006, 8, 4063;
102. c) Y.-X. Jia, J. Zhong, S.-F. Zhu, C.-M. Zhang, Q.-L. Zhou, Angew. Chem. 2007, 119, 5661;
103. Angew. Chem. Int. Ed. 2007, 46, 5565.
104. a) B. M. Trost, C. Müller, J. Am. Chem. Soc. 2008, 130, 2438;
105. b) G. Blay, I. Fernández, A. Monleón, J. R. Pedro, C. Vila, Org. Lett. 2009,11, 441.
106. a) N. A. Bumagin, V. V. Bykov, Tetrahedron 1997, 53, 14437;
107. b) T. B. Ayed, J. Villiéras, H. Amri, Tetrahedron 2000, 56, 805;
108. c) M. C. Walczak, R. S. Coleman, Org. Lett. 2005, 7, 2289;
109. d) Z. Lu, S. Ma, J. Org. Chem. 2006, 71, 2655.
110. CCDC-734380 (7) 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.