Asymmetric phase-transfer-catalyzed intramolecular N-alkylation of indoles and pyrroles: A combined experimental and theoretical investigation

Chemistry - A European Journal

Volumn 16, Issue 41, 2010, Pages 12462-12473

  Bandini, Marco ^a   Bottoni, Andrea ^a   Eichholzer, Astrid ^a   Miscione, Gian Pietro ^a   Stenta, Marco ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b EPFL   (Switzerland)

Author keywords

asymmetric catalysis; computational chemistry; indoles; Michael addition; phase transfer catalysis

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC PHASE; AZA-MICHAEL REACTION; ENANTIOSELECTIVE; EXPERIMENTAL INVESTIGATIONS; INDOLES; MECHANISTIC ASPECTS; MICHAEL ADDITIONS; N-ALKYLATION; NONBONDED INTERACTION; PHARMACOLOGICALLY ACTIVE COMPOUNDS; PHASE TRANSFER CATALYSIS; SYNTHETIC METHODOLOGY; THEORETICAL INVESTIGATIONS; WEAK INTERACTIONS;

ADDITION REACTIONS; ALKYLATION; COMPUTATIONAL CHEMISTRY; ESTERS; PLATINUM COMPOUNDS;

CATALYSIS;

INDOLE DERIVATIVE; PYRROLE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; THEORETICAL MODEL;

ALKYLATION; CATALYSIS; INDOLES; MODELS, THEORETICAL; PYRROLES; STEREOISOMERISM;

EID: 78249237550     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000560     Document Type: Article

References (90)

1. D. J. Faulkner, Nat. Prod. Rep. 2002, 19, 1 - 48
2. A. Kleeman, J. Engel, B. Kutscher, D. Reichert, Pharmaceutical Substances, 4th ed., Thieme, New York, 2001
3. J. Sundberg, Pyrroles and Their Benzoderivatives: Synthesis and Applications in Comprehensive Heterocyclic Chemistry, Vol. 4 (Eds.:, A. R. Katritzky, C. W. Rees,), Pergamon, Oxford, 1984, pp. 313 - 376
4. A. Joule, Indole and its Derivatives in Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, Vol. 10 (Ed.:, E. J. Thomas,), Thieme, Stuttgart, 2000; Chapter 10.13.
5. G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045 - 1075
6. R. Dalpozzo, G. Bartoli, Curr. Org. Synth. 2005, 2, 163 - 178
7. S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873 - 2920
8. G. W. Gribble, M. G. Saumier, E. T. Pelkey, T. L. S. Kishbaugh, Y. Liu, J. Jiang, H. A. Trujillo, D. J. Keavy, D. A. Davis, S. C. Conway, F. L. Switzer, S. Roy, R. A. Silva, J. A. Obaza-Nutatis, M. P. Sibi, N. V. Moskalev, T. C. Barden, L. Chang, W. M. Habeski, B. Pelcman, W. R. Sponholtz III, R. W. Chau, B. D. Allison, S. D. Garaas, M. S. Sinha, M. A. McGowan, M. R. Reese, K. S. Harpp, Curr. Org. Chem. 2005, 9, 1493 - 1519
9. S. Agarwal, S. Cämmerer, S. Filali, W. Froöhner, J. Knöll, M. P. Krahl, K. R. Reddy, H.-J. Knölker, Curr. Org. Chem. 2005, 9, 1601 - 1614
10. M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi, Synlett 2005, 1199 - 1222
11. G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875 - 2911
12. J. Campo, M. García-Valverde, S. Marcaccini, M. J. Rojo, T. Torroba, Org. Biomol. Chem. 2006, 4, 757 - 765.
13. K. A. Jørgensen, Synthesis 2003, 1117 - 1125
14. M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560 - 566
15. Angew. Chem. Int. Ed. 2004, 43, 550 - 556
16. M. Bandini, E. Emer, S. Tommasi, A. Umani-Ronchi, Eur. J. Org. Chem. 2006, 3527 - 3544
17. Y.-F. Sheng, A.-J. Zhang, X.-J. Zheng, S.-L. You, Chin. Org. Chem. 2008, 28, 605 - 616
18. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108, 2903 - 2915
19. S.-L. You, C. Quan, Z. Mi, Chem. Soc. Rev. 2009, 38, 2190 - 2201
20. M. Rueping, B. J. Nachtsheim, Beilstein J. Org. Chem. 2010, 6, DOI:.
21. Catalytic Asymmetric Friedel-Crafts Alkylations (Eds.:, M. Bandini, A. Umani-Ronchi,), Wiley-VCH, Weinheim, 2009.
22. D. A. Evans, K. R. Fandrick, Org. Lett. 2006, 8, 2249 - 2252
23. D. A. Evans, K. R. Fandrick, H.-J. Song, K. A. Scheidt, R. Xu, J. Am. Chem. Soc. 2007, 129, 10029 - 10041
24. G. Blay, I. Fernández, J. R. Pedro, C. Vila, Tetrahedron Lett. 2007, 48, 6731 - 6734
25. G. Blay, I. Fernández, J. R. Pedro, C. Vila, Org. Lett. 2007, 9, 2601 - 2604
26. Q. Kang, X.-J. Zheng, S.-L. You, Chem. Eur. J. 2008, 14, 3539 - 3542
27. M. Zeng, Q. Kang, Q. Kang, Q.-L. He, S.-L. You, Adv. Synth. Catal. 2008, 350, 2169 - 2173
28. Y.-F. Sheng, G.-Q. Li, Q. Kang, A.-J. Zhang, S.-L. You, Chem. Eur. J. 2009, 15, 3351 - 3354.
29. J. J. Vepsinen, S. Auriola, M. Tukiainen, N. Ropponen, Callaway, J. Planta Med. 2005, 71, 1049 - 1057
30. A. L. Williams, J. M. Srinivasan, J. N. Johnston, Org. Lett. 2006, 8, 6047 - 6049
31. S. Grüschow, L. C. Chang, Y. Mao, D. H. Sherman, J. Am. Chem. Soc. 2007, 129, 6470 - 6476, and references therein
32. M. B. Johansen, M. A. Kerr, Org. Lett. 2008, 10, 3497 - 3500
33. S. Chamberland, S. Grueschow, D. H. Sherman, R. M. Williams, Org. Lett. 2009, 11, 791 - 794.
34. D. Moffat, C.;J. Nichols, D. A. Riley, N.;S. Simpkins, Org. Biomol. Chem. 2005, 3, 2953 - 2975
35. E. Wincent, H. Shirani, J. Bergman, U. Rannug, T. Janosik, Bioorg. Med. Chem. 2009, 17, 1648 - 1653.
36. B. M. Trost, M. J. Krische, V. Berl, E. M. Grenzer, Org. Lett. 2002, 4, 2005 - 2008
37. For an analogous approach on pyrrole derivatives, see:, B. M. Trost, G. Dong, Chem. Eur. J. 2009, 15, 6910 - 6919
38. L. M. Stanley, J. F. Hartwig, Angew. Chem. 2009, 121, 7981 - 7984
39. Angew. Chem. Int. Ed. 2009, 48, 7841 - 7844.
40. H.-L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, Y.-C. Chen, Angew. Chem. 2009, 121, 5847 - 5850
41. Angew. Chem. Int. Ed. 2009, 48, 5737 - 5740
42. D. Enders, C. Wang, G. Raabe, Synthesis 2009, 4119 - 4124.
43. M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9786 - 9824
44. Angew. Chem. Int. Ed. 2009, 48, 9608 - 9644, and references therein
45. M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9697 - 9701
46. Angew. Chem. Int. Ed. 2009, 48, 9533 - 9537.
47. M. Bandini, A. Eichholzer, M. Tragni, A. Umani-Ronchi, Angew. Chem. 2008, 120, 3282 - 3285
48. Angew. Chem. Int. Ed. 2008, 47, 3238 - 3241.
49. F. Cafieri, E. Fattorusso, O. Tagliatela-Scafati, J. Nat. Prod. 1998, 61, 122 - 125, and references therein
50. K. G. Poullennec, D. Romo, J. Am. Chem. Soc. 2003, 125, 6344 - 6345
51. N. Nettekoven, J.-M. Plancher, H. Richter, O. Roche, S. Taylor, PCT Int. Appl. WO US 2007/0135416A1, 2007.
52. J. M. Bentley, P. Hebeisen, M. Muller, H. Richter, S. Roever, P. Mattei, S. Taylor, PCT Int. Appl. WO 2001-EP8520 20010724, 2002
53. R. K. Tiwari, A. K. Verma, A. K. Chhillar, D. Singh, J. Singh, V. K. Sankar, V. Yadav, G. L. Sharma, R. Chandra, Bioorg. Med. Chem. 2006, 14, 2747 - 2752.
54. J. Patel, N. Pelloux-LIon, F. Minassian, Y. VallIe, J. Org. Chem. 2005, 70, 9081 - 9084
55. J. Patel, N. Pelloux-LIon, F. Minassian, Y. VallIe, Tetrahedron Lett. 2006, 47, 5561 - 5563.
56. M. Bandini, A. Eichholzer, M. Monari, F. Piccinelli, A. Umani-Ronchi, Eur. J. Org. Chem. 2007, 2917 - 2920.
57. For general reviews see
58. A. Nelson, Angew. Chem. 1999, 111, 1685 - 1687
59. Angew. Chem. Int. Ed. 1999, 38, 1583 - 1585
60. B. Lygo, B. I. Andrews, Acc. Chem. Res. 2004, 37, 518 - 525
61. L.-W. Xu, C.-G. Xia, Eur. J. Org. Chem. 2005, 633 - 639, and references therein
62. A. Berkessel, H. Gröger, in Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005
63. T. Ooi, K. Maruoka, Aldrichimica Acta 2007, 40, 77 - 86
64. J. L. Vicario, D. Badia, L. Carrillo, Synthesis 2007, 2065 - 2092, and references therein
65. H. Pellissier, Tetrahedron 2007, 63, 9267 - 9331
66. K. Maruoka, Asymmetric Phase Transfer Catalysis, Wiley-VCH, Weinheim, 2008
67. K. Maruoka, Org. Process Res. Dev. 2008, 12, 679 - 697;
68. K. Maruoka, Synlett 2009, 652 - 652.
69. For representative examples see
70. K. Tajasu, S. Maiti, M. Ihara, Heterocycles 2003, 59, 51 - 55
71. S. Fustero, D. Jiménez, J. Moscardó, S. Catalán, C. del Pozo, Org. Lett. 2007, 9, 5283 - 5286
72. S. K. Bur, A. Pawda, Adv. Heterocycl. Chem. 2007, 94, 1 - 105
73. E. C. Carlson, L. K. Rathbone, H. Yang, N. D. Collet, R. G. Carter, J. Org. Chem. 2008, 73, 5155 - 5158
74. S. Fustero, J. Moscardó, D. Jiménez, M. D. Pérez-Carrion, M. Sanchez-Roselló, C. del Pozo, Chem. Eur. J. 2008, 14, 9868 - 9872
75. Asymmetric Synthesis of Nitrogen Heterocycles, (Ed.:, J. Royer,), Wiley-VCH, Weinheim, 2009, and references therein.
76. For representative examples
77. U.-H. Dolling, P. Davis, E. J. J. Grabowski, J. Am. Chem. Soc. 1984, 106, 446 - 447
78. D. L. Hughes, U.-H. Dolling, K. M. Ryan, E. F. Schoenewaldt, E. J. J. Grabowski, J. Org. Chem. 1987, 52, 4745 - 4752
79. E. J. Corey, F. Xu, M. C. Noe, J. Am. Chem. Soc. 1997, 119, 12414 - 12415
80. E. J. Corey, Y. Bo, J. Busch-Petersen, J. Am. Chem. Soc. 1998, 120, 13000 - 13001
81. T. Ooi, M. Kameda, M. Taniguchi, K. Maruoka, J. Am. Chem. Soc. 2004, 126, 9685 - 9694
82. A. Berkessel, M. Guixà, F. Schmidt, J. M. Neudörfl, J. Lex, Chem. Eur. J. 2007, 13, 4483 - 4498.
83. F. Bernardi, A. Bottoni, G. Tonachini, J. Chem. Soc. Perkin Trans. 2 1980, 467 - 470.
84. 2 group.
85. Y. Zhao, D. G. Truhlar, Acc. Chem. Res. 2008, 41, 157 - 167.
86. Y. Zhao, D. G. Truhlar, J. Phys. Chem. A 2004, 108, 6908 - 6918.
87. Y. Zhao, D. G. Truhlar, J. Phys. Chem. A 2005, 109, 5656 - 5667.
88. Y. Zhao, O. Tishchenko, D. G. Truhlar, J. Phys. Chem. B 2005, 109, 19046 - 19051.
89. Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
90. N. Godbout, D. R. Salahub, J. Andzelm, E. Wimmer, Can. J. Chem. 1992, 70, 560 - 571.