An organocatalytic, δ-regioselective, and highly enantioselective nucleophilic substitution of cyclic Morita-Baylis-Hillman alcohols with indoles

Angewandte Chemie - International Edition

Volumn 49, Issue 40, 2010, Pages 7294-7298

  Qiao, Zhen ^a   Shafiq, Zahid ^a   Liu, Li ^a   Yu, Zheng Bao ^a   Zheng, Qi Yu ^a   Wang, Dong ^a   Chen, Yong Jun ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

D regioselectivity; Indoles; Morita Baylis Hillman alcohols; Nucleophilic substitution; Organocatalysis

Indexed keywords

D REGIOSELECTIVITY; INDOLES; MORITA-BAYLIS-HILLMAN ALCOHOLS; NUCLEOPHILIC SUBSTITUTIONS; ORGANOCATALYSIS;

CATALYSIS; ENANTIOSELECTIVITY; REACTION KINETICS; REGIOSELECTIVITY;

RATE CONSTANTS;

EID: 77957348921     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201003131     Document Type: Article

References (99)

1. M. Bandini, M. Tragni, Org. Biomol. Chem. 2009, 7, 1501
2. N. Ljungdahl, N. Kann, Angew. Chem. 2009, 121, 652
3. Angew. Chem. Int. Ed. 2009, 48, 642
4. C.-J. Li; B. M. Trost, Proc. Natl. Acad. Sci. USA 2008, 105, 13197
5. B. M. Trost, Proc. Natl. Acad. Sci. USA 2008, 105, 13 197
6. J. A. McCubbin, H. Hosseini, O. V. Krokhin, J. Org. Chem. 2010, 75, 959.
7. For selected reviews on organocatalysis, see: a) A. Berkessel, H. Gröger, Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2004
8. B. List, Chem. Commun. 2006, 819
9. M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550
10. Angew. Chem. Int. Ed. 2006, 45, 1520
11. D.W. C. MacMillan, Nature 2008, 455, 304
12. S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178.
13. P. G. Cozzi, F. Benfatti, L. Zoli, Angew. Chem. 2009, 121, 1339
14. Angew. Chem. Int. Ed. 2009, 48, 1313
15. R. R. Shaikh, A. Mazzanti, M. Petrini, G. Bartoli, P. Melchiorre, Angew. Chem. 2008, 120, 8835
16. Angew. Chem. Int. Ed. 2008, 47, 8707
17. Q. X. Guo, Y. G. Peng, J. W. Zhang, L. Song, Z. Feng, L. Z. Gong, Org. Lett. 2009, 11, 4620
18. D. Enders, A. A. Narine, F. Toulgoat, T. Bisschops, Angew. Chem. 2008, 120, 5744
19. Angew. Chem. Int. Ed. 2008, 47, 5661.
20. Selected examples for metal-catalyzed enantioselective substitution of alcohols: a) M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9697
21. Angew. Chem. Int. Ed. 2009, 48, 9533
22. B. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314
23. Y. Yamashita, A. Gopalarathnam, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 7508
24. H. Matsuzawa, Y. Miyake, Y. Nishibayashi, Angew. Chem. 2007, 119, 6608
25. Angew. Chem. Int. Ed. 2007, 46, 6488.
26. Selected examples for the Friedel-Craft reactions of chiral alcohols: a) D. Stadler, T. Bach, Angew. Chem. 2008, 120, 7668
27. Angew. Chem. Int. Ed. 2008, 47, 7557
28. F. Mühlthau,D. Stadler, A. Goeppert, G. A. Olah, G. K. S. Prakash, T. Bach, J. Am. Chem. Soc. 2006, 128, 9668.
29. D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811
30. D. Basavaiah, A. J. Rao, R. J. Reddy, Chem. Soc. Rev. 2007, 36, 1581
31. G. Masson, C. Housseman, J. Zhu, Angew. Chem. 2007, 119, 4698
32. Angew. Chem. Int. Ed. 2007, 46, 4614
33. V. Singh, S. Batra, Tetrahedron 2008, 64, 4511.
34. Selected examples for the conjugate addition of MBH alcohols: a) L. A. Paquette, R. R. Rothhaar, M. Isaac, L. M. Rogers, R. D. Rogers, J. Org. Chem. 1998, 63, 5463
35. W. Wang, M. Yu, Tetrahedron Lett. 2004, 45, 7141
36. S. Nag, G. P. Yadav, P. R. Maulik, S. Batra, Synthesis 2007, 911
37. R. Pathak, S. Batra, Tetrahedron 2007, 63, 9448
38. S. Nag, R. Pathak, M. Kumar, P. K. Shukla, S. Batra, Bioorg. Med. Chem. Lett. 2006, 16, 3824.
39. Selected examples for a-allylic substitution of MBH alcohols: a) K. Y. Lee, H. S. Lee, J. N. Kim, Bull. Korean Chem. Soc. 2008, 29. 1099
40. X. Zhang, W. Rao, S. P. W. H. Chan, Org. Biomol. Chem. 2009, 7, 4186
41. C. Wu, L. Liu, D. Wang, Y. J. Chen, Tetrahedron Lett. 2009, 50, 3786; selected examples for g-allylic substitution of MBH alcohols
42. L. Navarre, S. Darses, J. P. Genet, Chem. Commun. 2004, 1108
43. M. L. Kantam, K. B. Shiva Kumar, B. Sreedhar, J. Org. Chem. 2008, 73, 320
44. L. R. Reddy, B. Hu, M. Prashad, K. Prasad, Angew. Chem. 2009, 121, 178
45. Angew. Chem. Int. Ed. 2009, 48, 172.
46. B. M. Trost, O. R. Thiel, H. C. Tsui, J. Am. Chem. Soc. 2002, 124, 11616
47. B. M. Trost, O. R. Thiel, H. C. Tsui, J. Am. Chem. Soc. 2003, 125, 13155
48. B. M. Trost, M. R. Machacek, H. C. Tsui, J. Am. Chem. Soc. 2005, 127, 7014
49. B. M. Trost, M. K. Brennan, Org. Lett. 2007, 9, 3961
50. T. Nemoto, T. Fukuyama, E. Yamamoto, S. Tamura, T. Fukuda, T. Matsumoto, Y. Akimoto, Y. Hamada, Org. Lett. 2007, 9, 927
51. C. G. Chen, X. L. Hou, L. Pu, Org. Lett. 2009, 11, 2073.
52. C.W. Cho, M. J. Krische, Angew. Chem. 2004, 116, 6857
53. Angew. Chem. Int. Ed. 2004, 43, 6689
54. Y. Q. Jiang, Y. L. Shi, M. Shi, J. Am. Chem. Soc. 2008, 130, 7202
55. D. J. V. C. van Steenis, T. Marcelli, M. Lutz, A. L. Spek, J. H. van Maarseveen, H. Hiemstra, Adv. Synth. Catal. 2007, 349, 281
56. H. L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, Y. C. Chen, Angew. Chem. 2009, 121, 5847
57. Angew. Chem. Int. Ed. 2009, 48, 5737
58. H. L. Cui, J. Peng, X. Feng,W. Du, K. Jiang, Y. C. Chen, Chem. Eur. J. 2009, 15, 1574
59. K. Jiang, J. Peng, H. L. Cui, Y. C. Chen, Chem. Commun. 2009, 3955
60. J. N. Kim, H. J. Lee, J. H. Gong, Tetrahedron Lett. 2002, 43, 9141
61. Y. S. Du, X. L. Han, X. Y. Lu, Tetrahedron Lett. 2004, 45, 4967
62. P. V. Ramachandran, S. Madhi, L. Bland-Berry, M. V. R. Reddy, M. J. O'Donnell, J. Am. Chem. Soc. 2005, 127, 13450.
63. A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416
64. P. Melchiorre, Angew. Chem. 2008, 120, 6232
65. Angew. Chem. Int. Ed. 2008, 47, 6138.
66. For a review on modified cinchona alkaloid, see: a) S. K. Tian, Y. Chen, J. Hang, L. Tang, P. McDaid, L. Deng, Acc. Chem. Res. 2004, 37, 621.
67. For selected asymmetric reactions catalyzed by cinchona alkaloid C, see: b)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
68. Angew. Chem. Int. Ed. 2007, 46, 389
69. J. W. Xie, L. Yue, W. Chen, W. Du, J. Zhu, J. G. Deng, Y.-C. Chen, Org. Lett. 2007, 9, 413
70. d)W. Chen,W. Du, Y. Z. Duan, Y. Wu, S. Y. Yang, Y. C. Chen, Angew. Chem. 2007, 119, 7811
71. Angew. Chem. Int. Ed. 2007, 46, 7667
72. X. F. Li, L. F. C, Cun. X. Lian, L. Zhong, Y. C. Chen, J. Liao, J. Zhu, J. G. Deng, Org. Biomol. Chem. 2008, 6, 349
73. X.Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2008, 130, 6070
74. C. M. Reisinger, X. Wang, B. List, Angew. Chem. 2008, 120, 8232
75. Angew. Chem. Int. Ed. 2008, 47, 8112
76. X. Lu, Y. Liu, B. Sun, B. Cindric, L. Deng, J. Am. Chem. Soc. 2008, 130, 8134
77. X. Lu, L. Deng, Angew. Chem. 2008, 120, 7824
78. Angew. Chem. Int. Ed. 2008, 47, 7710
79. R. P. Singh, K. Bartelson, Y.Wang, H. Su, X. J. Lu, L. Deng, J. Am. Chem. Soc. 2008, 130, 2422
80. F. Pesciaioli, F. D. Vincentiis, P. Galzerano, G. Bencivenni, G. Bartoli, A. Mazzanti, P. Melchiorre, Angew. Chem. 2008, 120, 8831
81. Angew. Chem. Int. Ed. 2008, 47, 8703
82. lM.W. Paixão, N. Holub, C. Vila, M. Nielsen, K. A. Jørgensen, Angew. Chem. 2009, 121, 7474
83. Angew. Chem. Int. Ed. 2009, 48, 7338.
84. S. Lakhdar, M. Westermaier, F. Terrier, R. Goumont, T. Boubaker, A. R. Ofial, H. Mayr, J. Org. Chem. 2006, 71, 9088
85. M. Westermaier, H. Mayr, Chem. Eur. J. 2008, 14, 1638.
86. CCDC 775440 (4d) contains 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.
87. Z. Shafiq, Z. Qiao, L. Liu, Q.-Y. Zheng, D. Wang, Y. J. Chen, Synlett 2009, 2965
88. Y. L. Liu, L. Liu, D. Wang, Y. J. Chen, Tetrahedron 2009, 65, 3473
89. Z. Shafiq, L. Liu, Z. Liu, D. Wang, Y. J. Chen, Org. Lett. 2007, 9, 2525.
90. See the Supporting Information. ESI-MS analyses for studies on the mechanism of iminium catalysis, see: a) Z. J. Wu, S.W. Luo, J. W. Xie, X. Y. Xu, D. M. Fang, G. L. Zhang, J. Am. Soc. Mass Spectrom. 2007, 18, 2074
91. W. Schrader, P. P. Handayani, J. Zhou, B. List, Angew. Chem. 2009, 121, 1491
92. Angew. Chem. Int. Ed. 2009, 48, 1463.
93. For the asymmetric Friedel-Crafts reaction of indoles with cycloenones, see: a) G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403
94. W. Chen,W. Du, L. Yue, R. Li, Y.Wu, L.-S. Ding, Y. C. Chen, Org. Biomol. Chem. 2007, 5, 816
95. H. Y. Tang, A. D. Lu, Z. H. Zhou, G. F. Zhao, L. N. He, C. C. Tang, Eur. J. Org. Chem. 2008, 1406.
96. for other selected examples for the addition of aromatic compounds to cycloenones, see: d) K. Manabe, N. Aoyama, S. Kobayasgi, Adv. Synth. Catal. 2001, 343, 174.
97. H. Firouzabadi, N. Iranpoor, A. A. Jafari, J. Mol. Catal. A 2006, 244, 168
98. W. D. Li, X. W. Wang, Org. Lett. 2007, 9, 1211
99. M. A. Grundl, A. Kaster, E. D. Beaulieu, D. Trauner, Org. Lett. 2006, 8, 5429.