Two-step synthesis of multi-substituted amines by using an N-methoxy group as a reactivity control element

Chemistry - A European Journal

Volumn 20, Issue 26, 2014, Pages 8210-8216

  Yoritate, Makoto ^a   Meguro, Tatsuhiko ^a   Matsuo, Naoya ^a   Shirokane, Kenji ^a   Sato, Takaaki ^a   Chida, Noritaka ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

amides; nitrogen; nucleophilic addition; piperidine; reactivity control

Indexed keywords

ADDITION REACTIONS; AMINES; NITROGEN; SYNTHESIS (CHEMICAL);

COUPLING REACTION; ELECTROPHILICITY; NUCLEOPHILIC ADDITIONS; NUCLEOPHILICITIES; PIPERIDINE; REACTIVITY CONTROL; TWO-STEP PROCESS; TWO-STEP SYNTHESIS;

AMIDES;

EID: 84902993761     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201402231     Document Type: Article

References (129)

1. S. Robin, G. Rousseau, Tetrahedron 1998, 54, 13681-13736; for selected examples of electrophilic cyclization of N-alkoxyamides, see
2. G. Rajendra, M. J. Miller, Tetrahedron Lett. 1985, 26, 5385-5388
3. G. Rajendra, M. J. Miller, J. Org. Chem. 1987, 52, 4471-4477
4. G. Rajendra, M. J. Miller, Tetrahedron Lett. 1987, 28, 6257-6260
5. R. M. Williams, G. F. Miknis, Tetrahedron Lett. 1990, 31, 4297-4300
6. G. F. Miknis, R. M. Williams, J. Am. Chem. Soc. 1993, 115, 536-547
7. M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, J. Chem. Soc. Chem. Commun. 1995, 237-238
8. S.-S. Jew, K.-H. Cha, S.-D. Kang, Y.-H. Woo, H.-O. Kim, H.-G. Park, Heterocycles 1999, 50, 677-680
9. M. Tiecco, L. Testaferri, F. Marini, S. Sternativo, L. Bagnoli, C. Santi, A. Temperini, Tetrahedron: Asymmetry 2001, 12, 1493-1502
10. B. Janza, A. Studer, Synthesis 2002, 2117-2123
11. H. Trabulsi, R. Guillot, G. Rousseau, Eur. J. Org. Chem. 2010, 5884-5896.
12. S. Nahm, S. M. Weinreb, Tetrahedron Lett. 1981, 22, 3815-3818.
13. Part of this work was published as a preliminary account, see:, K. Shirokane, T. Wada, M. Yoritate, R. Minamikawa, N. Takayama, T. Sato, N. Chida, Angew. Chem. 2014, 126, 522-526
14. Angew. Chem. Int. Ed. 2014, 53, 512-516.
15. J. W. Daly, B. Witkop, T. Tokuyama, T. Nishikawa, I. L. Karle, Helv. Chim. Acta 1977, 60, 1128-1140
16. J. W. Daly, G. B. Brown, M. Mensah-Dwumah, C. W. Myers, Toxicon 1978, 16, 163-188
17. M. Mensah-Dwumah, J. W. Daly, Toxicon 1978, 16, 189-194
18. C. Souccar, M. A. Maleque, J. W. Daly, E. X. Albuquerque, Fed. Am. Soc. Exp. Biol. Fed. Proc. 1982, 41, 1299
19. J. W. Daly, Y. Nishizawa, M. W. Edwards, J. A. Waters, R. S. Aronstam, Neurochem. Res. 1991, 16, 489-500.
20. For a recent review on cylindricines, see:, S. M. Weinreb, Chem. Rev. 2006, 106, 2531-2549.
21. For a recent review on macroline, sarpagine, and ajmaline-related indole alkaloids including kouamine (11), see:, S. E. Lewis, Tetrahedron 2006, 62, 8655-8681.
22. We reported concise synthesis of 12 in two steps from commercially available 4-pentenoic acid, see ref. [3]. Wardrop also reported a three-step synthesis of 12 from ethyl pentenoate, see:, D. J. Wardrop, M. V. Yermolina, E. G. Bowen, Synthesis 2012, 44, 1199-1207.
23. B. E. Maryanoff, H.-C. Zhang, J. H. Cohen, I. J. Turchi, C. A. Maryanoff, Chem. Rev. 2004, 104, 1431-1628; for coupling reactions of an N-alkoxyamide with an aldehyde or its derivative, see
24. J. Nakano, T. Ichiyanagi, H. Ohta, Y. Ito, Tetrahedron Lett. 2003, 44, 2853-2856
25. C. M. Marson, S. Pucci, Tetrahedron Lett. 2004, 45, 9007-9010
26. X. Zheng, X. Wang, J. Chang, K. Zhao, Synlett 2006, 3277-3283
27. X. Zheng, J. Chang, K. Zhao, Synthesis 2008, 1345-1350.
28. D. Seebach, Angew. Chem. 2011, 123, 99-105
29. Angew. Chem. Int. Ed. 2011, 50, 96-101
30. T. Murai, Y. Mutoh, Chem. Lett. 2012, 41, 2-8
31. V. Pace, W. Holzer, Aust. J. Chem. 2013, 66, 507-510.
32. K. Shirokane, Y. Kurosaki, T. Sato, N. Chida, Angew. Chem. 2010, 122, 6513-6516
33. Angew. Chem. Int. Ed. 2010, 49, 6369-6372
34. Y. Yanagita, H. Nakamura, K. Shirokane, Y. Kurosaki, T. Sato, N. Chida, Chem. Eur. J. 2013, 19, 678-684; Vincent/Kouklovsky and Helmchen independently reported the excellent nucleophilic addition to N-alkoxyamides, see
35. G. Vincent, R. Guillot, C. Kouklovsky, Angew. Chem. 2011, 123, 1386-1389
36. Angew. Chem. Int. Ed. 2011, 50, 1350-1353
37. G. Vincent, D. Karila, G. Khalil, P. Sancibrao, D. Gori, C. Kouklovsky, Chem. Eur. J. 2013, 19, 9358-9365
38. M. Jäkel, J. Qu, T. Schnitzer, G. Helmchen, Chem. Eur. J. 2013, 19, 16746-16755. For the pioneer work, see
39. H. Iida, Y. Watanabe, C. Kibayashi, J. Am. Chem. Soc. 1985, 107, 5534-5535.
40. M. P. DeNinno, C. Eller, Tetrahedron Lett. 1997, 38, 6545-6548
41. S. M. Denton, A. Wood, Synlett 1999, 55-56
42. Y.-G. Suh, D.-Y. Shin, J.-K. Jung, S.-H. Kim, Chem. Commun. 2002, 1064-1065
43. T. Murai, Y. Mutoh, Y. Ohta, M. Murakami, J. Am. Chem. Soc. 2004, 126, 5968-5969
44. T. Murai, F. Asai, J. Am. Chem. Soc. 2007, 129, 780-781
45. O. Tomashenko, V. Sokolov, A. Tomashevskiy, H. A. Buchholz, U. Welz-Biermann, V. Chaplinski, A. de Meijere, Eur. J. Org. Chem. 2008, 5107-5111
46. K.-J. Xiao, J.-M. Luo, K.-Y. Ye, Y. Wang, P.-Q. Huang, Angew. Chem. 2010, 122, 3101-3104
47. Angew. Chem. Int. Ed. 2010, 49, 3037-3040
48. G. Bélanger, G. O'Brien, R. Larouche-Gauthier, Org. Lett. 2011, 13, 4268-4271
49. J. W. Medley, M. Movassaghi, Angew. Chem. 2012, 124, 4650-4654
50. Angew. Chem. Int. Ed. 2012, 51, 4572-4576
51. K.-J. Xiao, A.-E. Wang, P.-Q. Huang, Angew. Chem. 2012, 124, 8439-8442
52. Angew. Chem. Int. Ed. 2012, 51, 8314-8317
53. S. Bonazzi, B. Cheng, J. S. Wzorek, D. A. Evans, J. Am. Chem. Soc. 2013, 135, 9338-9341
54. K.-J. Xiao, J.-M. Luo, X.-E. Xia, Y. Wang, P.-Q. Huang, Chem. Eur. J. 2013, 19, 13075-13086
55. K.-J. Xiao, Y. Wang, Y.-H. Huang, X.-G. Wang, P.-Q. Huang, J. Org. Chem. 2013, 78, 8305-8311.
56. B. Hardegger, S. Shatzmiller, Helv. Chim. Acta 1976, 59, 2765-2767
57. R. Plate, R. H. M. van Hout, H. Behm, H. C. J. Ottenheijm, J. Org. Chem. 1987, 52, 555-560
58. A. Padwa, D. C. Dean, J. Org. Chem. 1990, 55, 405-406
59. P. H. H. Hermkens, J. H. van Maarseveen, P. L. H. M. Cobben, H. C. J. Ottenheijm, C. G. Kruse, H. W. Scheeren, Tetrahedron 1990, 46, 833-846
60. M. Tiecco, L. Testaferri, M. Tingoli, L. Bagnoli, J. Chem. Soc. Chem. Commun. 1995, 235-236
61. M. C. McMills, D. L. Wright, J. D. Zubkowski, E. J. Valente, Tetrahedron Lett. 1996, 37, 7205-7208
62. R. Grigg, Z. Rankovic, M. Thoroughgood, Tetrahedron 2000, 56, 8025-8032
63. T. Yamashita, N. Kawai, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2005, 127, 15038-15039
64. H. A. Dondas, R. Grigg, J. Markandu, T. Perrior, T. Suzuki, S. Thibault, W. A. Thomas, M. Thornton-Pett, Tetrahedron 2002, 58, 161-173
65. R. Ando, G. Li, J. Song, W. Liao, R. Ma, S.-H. Chen, Z. Peng, Lett. Org. Chem. 2006, 3, 455-458
66. H. Nemoto, R. Ma, T. Kawamura, M. Kamiya, M. Shibuya, J. Org. Chem. 2006, 71, 6038-6043
67. X. Zheng, X. Wang, J. Chang, K. Zhao, Synlett 2006, 3277-3283
68. H. Nemoto, R. Ma, H. Moriguchi, T. Kawamura, M. Kamiya, M. Shibuya, J. Org. Chem. 2007, 72, 9850-9853
69. S. K. Jackson, A. Karadeolian, A. B. Driega, M. A. Kerr, J. Am. Chem. Soc. 2008, 130, 4196-4201
70. Y. Kurosaki, K. Shirokane, T. Oishi, T. Sato, N. Chida, Org. Lett. 2012, 14, 2098-2101; additions and corrections
71. Y. Kurosaki, K. Shirokane, T. Oishi, T. Sato, N. Chida, Org. Lett. 2012, 14, 2430.
72. S. T.-C. Eey, M. J. Lear, Org. Lett. 2010, 12, 5510-5513.
73. W. N. Speckamp, H. Hiemstra, Tetrahedron 1985, 41, 4367-4416
74. W. N. Speckamp, M. J. Moolenaar, Tetrahedron 2000, 56, 3817-3856
75. J. Royer, M. Bonin, L. Micouin, Chem. Rev. 2004, 104, 2311-2352.
76. H. Hiemstra, H. P. Fortgens, W. N. Speckamp, Tetrahedron Lett. 1985, 26, 3155-3158
77. C. Y. Hong, N. Kado, L. E. Overman, J. Am. Chem. Soc. 1993, 115, 11028-11029
78. D. A. Heerding, C. Y. Hong, N. Kado, G. C. Look, L. E. Overman, J. Org. Chem. 1993, 58, 6947-6948.
79. H. Hiemstra, M. H. A. M. Sno, R. J. Vijn, W. N. Speckamp, J. Org. Chem. 1985, 50, 4014-4020
80. C. Agami, D. Bihan, R. Morgentin, C. Puchot-Kadouri, Synlett 1997, 799-800
81. M. Suginome, T. Iwanami, Y. Ito, J. Org. Chem. 1998, 63, 6096-6097
82. C. Agami, D. Bihan, L. Hamon, C. Puchot-Kadouri, Tetrahedron 1998, 54, 10309-10316
83. H. Huang, T. F. Spande, J. S. Panek, J. Am. Chem. Soc. 2003, 125, 626-627
84. S. S. Kinderman, R. de Gelder, J. H. van Maarseveen, H. E. Schoemaker, H. Hiemstra, F. P. J. T. Rutjes, J. Am. Chem. Soc. 2004, 126, 4100-4101
85. S. M. Amorde, A. S. Judd, S. F. Martin, Org. Lett. 2005, 7, 2031-2033
86. S. M. Amorde, I. T. Jewett, S. F. Martin, Tetrahedron 2009, 65, 3222-3231.
87. B. M. Trost, Science 1991, 254, 1471-1477
88. A. Boudier, L. O. Bromm, M. Lotz, P. Knochel, Angew. Chem. 2000, 112, 4584-4606
89. Angew. Chem. Int. Ed. 2000, 39, 4414-4435
90. P. A. Wender, M. P. Croatt, B. Witulski, Tetrahedron 2006, 62, 7505-7511
91. B. M. Trost, G. Dong, Nature 2008, 456, 485-488
92. N. Z. Burns, P. S. Baran, R. W. Hoffmann, Angew. Chem. 2009, 121, 2896-2910
93. Angew. Chem. Int. Ed. 2009, 48, 2854-2867
94. I. S. Young, P. S. Baran, Nat. Chem. 2009, 1, 193-205
95. N. A. Afagh, A. K. Yudin, Angew. Chem. 2010, 122, 270-320
96. Angew. Chem. Int. Ed. 2010, 49, 262-310.
97. D. J. Calderwood, R. V. Davies, P. Rafferty, H. L. Twigger, H. M. Whelan, Tetrahedron Lett. 1997, 38, 1241-1244
98. S. Wiedemann, I. Marek, A. de Meijere, Synlett 2002, 0879-0882
99. Q. Xia, B. Ganem, Org. Lett. 2001, 3, 485-487
100. Q. Xia, B. Ganem, Tetrahedron Lett. 2002, 43, 1597-1598
101. W. S. Bechara, G. Pelletier, A. B. Charette, Nat. Chem. 2012, 4, 228-234
102. K.-J. Xiao, A.-E. Wang, Y.-H. Huang, P.-Q. Huang, Asian J. Org. Chem. 2012, 1, 130-132
103. Y. Oda, T. Sato, N. Chida, Org. Lett. 2012, 14, 950-953
104. Y. Inamoto, Y. Kaga, Y. Nishimoto, M. Yasuda, A. Baba, Org. Lett. 2013, 15, 3452-3455. Magnus reported sequential nucleophilic addition to carbamates in the total synthesis of kopsidasine, see
105. P. Magnus, A. H. Payne, L. Hobson, Tetrahedron Lett. 2000, 41, 2077-2081
106. P. Magnus, L. Gazzard, L. Hobson, A. H. Payne, T. J. Rainey, N. Westlund, V. Lynch, Tetrahedron 2002, 58, 3423-3443.
107. P. C. Wailes, H. Weigold, J. Organomet. Chem. 1970, 24, 405-411
108. D. W. Hart, J. Schwartz, J. Am. Chem. Soc. 1974, 96, 8115-8116.
109. D. J. A. Schedler, A. G. Godfrey, B. Ganem, Tetrahedron Lett. 1993, 34, 5035-5038
110. D. J. A. Schedler, J. Li, B. Ganem, J. Org. Chem. 1996, 61, 4115-4119
111. S. Bower, K. A. Kreutzer, S. L. Buchwald, Angew. Chem. 1996, 108, 1662-1664
112. Angew. Chem. Int. Ed. Engl. 1996, 35, 1515-1516
113. J. M. White, A. R. Tunoori, G. I. Georg, J. Am. Chem. Soc. 2000, 122, 11995-11996
114. J. T. Spletstoser, J. M. White, A. R. Tunoori, G. I. Georg, J. Am. Chem. Soc. 2007, 129, 3408-3419
115. Y. Motoyama, M. Aoki, N. Takaoka, R. Aoto, H. Nagashima, Chem. Commun. 2009, 1574-1576
116. R. Kuwano, M. Takahashi, Y. Ito, Tetrahedron Lett. 1998, 39, 1017-1020
117. G. Barbe, A. B. Charette, J. Am. Chem. Soc. 2008, 130, 18-19
118. S. Zhou, K. Junge, D. Addis, S. Das, M. Beller, Angew. Chem. 2009, 121, 9671-9674
119. Angew. Chem. Int. Ed. 2009, 48, 9507-9510
120. S. Das, D. Addis, S. Zhou, K. Junge, M. Beller, J. Am. Chem. Soc. 2010, 132, 1770-1771
121. G. Pelletier, W. S. Bechara, A. B. Charette, J. Am. Chem. Soc. 2010, 132, 12817-12819
122. S.-H. Xiang, J. Xu, H.-Q. Yuan, P.-Q. Huang, Synlett 2010, 1829-1832
123. S. Das, D. Addis, K. Junge, M. Beller, Chem. Eur. J. 2011, 17, 12186-12192
124. C. Cheng, M. Brookhart, J. Am. Chem. Soc. 2012, 134, 11304-11307
125. J. T. Reeves, Z. Tan, M. A. Marsini, Z. S. Han, Y. Xu, D. C. Reeves, H. Lee, B. Z. Lu, C. H. Senanayake, Adv. Synth. Catal. 2013, 355, 47-52
126. T. Zhang, Y. Zhang, W. Zhang, M. Luo, Adv. Synth. Catal. 2013, 355, 2775-2780
127. B. Ravinder, R. S. Reddy, P. A. Reddy, R. Bandichhor, Tetrahedron Lett. 2013, 54, 4908-4913.
128. R. V. Stevens, Acc. Chem. Res. 1984, 17, 289-296
129. P. Deslonchamps, in Stereolectronics Effects in Organic Chemistry, Pergamon, New York, 1983, Chapter 6.