Chemoselective reductive nucleophilic addition to tertiary amides, secondary amides, and N-methoxyamides

Chemistry - A European Journal

Volumn 20, Issue 52, 2014, Pages 17565-17571

  Nakajima, Minami ^a   Oda, Yukiko ^a   Wada, Takamasa ^a   Minamikawa, Ryo ^a   Shirokane, Kenji ^a   Sato, Takaaki ^a   Chida, Noritaka ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Amides; Chemoselectivity; Nitrogen; Nucleophilic addition; Sequential reactions

Indexed keywords

AMIDES; FUNCTIONAL GROUPS; NITROGEN; SYNTHESIS (CHEMICAL);

CHEMO-SELECTIVITY; CLASSICAL METHODS; CONCISE SYNTHESIS; NUCLEOPHILIC ADDITIONS; ORGANIC SYNTHESIS; REACTION CONDITIONS; SECONDARY AMIDES; SEQUENTIAL REACTION;

ADDITION REACTIONS;

EID: 84920155707     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201404648     Document Type: Article

References (83)

1. a) B. M. Trost, Science 1991, 254, 1471-1477
2. b) A. Boudier, L O. Bromm, M. Lotz, P. Knochel, Angew. Chem. Int. Ed. 2000, 39, 4414-4435
3. Angew. Chem. 2000, 112, 4584-4606
4. c) P. A. Wender, M. P. Croatt, B. Witulski, Tetrahedron 2006, 62, 7505-7511
5. d) B. M. Trost, G. Dong, Nature 2008, 456, 485-488
6. e) N. Z. Burns, P. S. Baran, R. W. Hoffmann, Angew. Chem. Int. Ed. 2009, 48, 2854-2867
7. Angew. Chem. 2009, 121, 2896-2910
8. f) I. S. Young, P.S. Baran, Nat. Chem. 2009, 1, 193-205
9. g) N. A. Afagh, A. K. Yudin, Angew. Chem. Int. Ed. 2010, 49, 262-310
10. Angew. Chem. 2010, 122, 270-320.
11. For reviews and perspectives on nucleophilic additions to amides, see: a) D. Seebach, Angew. Chem. Int. Ed. 2011, 50, 96-101
12. Angew. Chem. 2011, 123, 99-105
13. b) T. Murai, Y. Mutoh, Chem. Lett. 2012, 41, 2-8
14. c) V. Pace, W. Holzer, Aust. J. Chem. 2013, 66, 507-510
15. d) T. Sato, N. Chida, Org. Biomol. Chem. 2014, 12, 3147-3150.
16. For selected examples of non-chemoselective nucleophilic additions to amides, see: a) M. P. DeNinno, C. Eller, Tetrahedron Lett. 1997, 38, 6545-6548
17. b) S. M. Denton, A. Wood, Synlett 1999, 55-56
18. c) Y.-G. Suh, D.-Y. Shin, J.-K. Jung, S.-H. Kim, Chem. Commun. 2002, 1064-1065
19. d) T. Murai, Y. Mutoh, Y. Ohta, M. Murakami, J. Am. Chem. Soc. 2004, 126, 5968-5969
20. e) T. Murai, F. Asai, J. Am. Chem. Soc. 2007, 129, 780-781
21. f) O. Tomashenko, V. Sokolov, A. Tomashevskiy, H. A. Buchholz, U. Welz-Biermann, V. Chaplinski, A. de Meijere, Eur. J. Org. Chem. 2008, 5107-5111
22. g) K.-J. Xiao, J.-M. Luo, K.-Y. Ye, Y. Wang, P.-Q. Huang, Angew. Chem. Int. Ed. 2010, 49, 3037-3040
23. Angew. Chem. 2010, 122, 3101-3104
24. h) K.-J. Xiao, Y Wang, K.-Y Ye, P.-Q. Huang, Chem. Eur. J. 2010, 16, 12792-12796
25. i) G. Bélanger, G. O'Brien, R. Larouche-Gauthier, Org. Lett. 2011, 13, 4268-4271
26. j) J. W. Medley, M. Movassaghi, Angew. Chem. Int. Ed. 2012, 51, 4572-4576
27. Angew. Chem. 2012, 124, 4650-4654
28. k) K.-J. Xiao, A.-E. Wang, P.-Q. Huang, Angew. Chem. Int. Ed. 2012, 51, 8314-8317
29. Angew. Chem. 2012, 124, 8439-8442
30. l) S. Bonazzi, B. Cheng, J. S. Wzorek, D. A. Evans, J. Am. Chem. Soc. 2013, 135, 9338-9341
31. m) K.-J. Xiao, J.-M. Luo, X.-E. Xia, Y Wang, P.-Q. Huang, Chem. Eur. J. 2013, 19, 13075-13086
32. n) K.-J. Xiao, Y Wang, Y.-H. Huang, X.-G. Wang, P.-Q. Huang, J. Org. Chem. 2013, 78, 8305-8311
33. o) H.-Q. Deng, X.-Y Qian, Y-X. Li, J.-F. Zheng, L. Xie, P.-Q. Huang, Org. Chem. Front. 2014, 1, 258-266.
34. We reported the non-chemoselective nucleophilic addition to N-alkox-yamides, see: a) K. Shirokane, Y Kurosaki, T. Sato, N. Chida, Angew. Chem. Int. Ed. 2010, 49, 6369-6372
35. Angew. Chem. 2010, 122, 6513-6516
36. b) Y Yanagita, H. Nakamura, K. Shirokane, Y Kurosaki, T. Sato, N. Chida, Chem. Eur. J. 2013, 19, 678-684
37. Vincent/Kouklovsky and Helmchen independently reported the excellent nucleophilic addition to N-alkoxyamides, see: c) G. Vincent, R. Guillot, C Kouklovsky, Angew. Chem. Int. Ed. 2011, 50, 1350-1353
38. Angew. Chem. 2011, 123, 1386-1389
39. d) G. Vincent, D. Karila, G. Khalil, P. Sancibrao, D. Gori, C Kouklovsky, Chem. Eur. J. 2013, 19, 9358-9365
40. e) M. Jäkel, J. Qu, T. Schnitzer, G. Helmchen, Chem. Eur. J. 2013, 19, 16746-16755
41. Kibayashi reported excellent pioneering work in the total synthesis of natural products, see: f) H. Iida, Y Watanabe, C Kibayashi, J. Am. Chem. Soc. 1985, 107, 5534-5535.
42. Related nucleophilic additions to esters with higher electrophilicity than amides were reported. For selected examples of transformation of acyclic esters to ethers via a-acetoxy ethers, see: a)V. H. Dahanukar, S.D. Rychnovsky, J. Org. Chem. 1996, 61, 8317-8320
43. b) D.J. Kopecky, S.D. Rychnovsky, J. Org. Chem. 2000, 65, 191-198
44. c) I. Kadota, A. Ohno, K. Matsuda, Y Yamamoto, J. Am. Chem. Soc. 2001, 123, 6702-6703.
45. For selected recent reviews on amide-bond formation, see: a) J. M. Humphrey, A. R. Chamberlin, Chem. Rev. 1997, 97, 2243-2266
46. b) F. Albericio, R. Chinchilla, D. J. Dodsworth, C. Nájera, Org. Prep. Proced. Int. 2001, 33, 203-313
47. c) S.-Y Han, Y.-A. Kim, Tetrahedron 2004, 60, 2447-2467
48. d) C. A. G. N. Montalbetti, V. Falque, Tetrahedron 2005, 61, 10827-10852
49. e) E. Valeur, M. Bradley, Chem. Soc. Rev. 2009, 38, 606-631.
50. For chemoselective transformations of amide carbonyl groups by C-C bond formation, see: a) D.J. Calderwood, R. V. Davies, P. Rafferty, H. L. Twigger, H. M. Whelan, Tetrahedron Lett. 1997, 38, 1241-1244
51. b) S. Wiedemann, I. Marek, A. de Meijere, Synlett 2002, 879-882
52. c) W. S. Bechara, G. Pelletier, A. B. Charette, Nat. Chem. 2012, 4, 228-234
53. d) K.-J. Xiao, A.-E. Wang, Y.-H. Huang, P.-Q. Huang, Asian J. Org. Chem. 2012, 1, 130-132
54. e) M. Yoritate, T. Meguro, N. Matsuo, K. Shirokane, T. Sato, N. Chida, Chem. Eur. J. 2014, 20, 8210-8216
55. f) P.-Q. Huang, W. Ou, K.-J. Xiao, A.-E. Wang, Chem. Commun. 2014, 50, 8761-8763
56. Baba reported the chemoselective nucleophilic addition to sulfonylamides, see: g) Y. Inamoto, Y. Kaga, Y. Nishimoto, M. Yasuda, A. Baba, Org. Lett. 2013, 15, 3452-3455
57. Magnus reported the sequential nucleophilic addition to carbamates in the total synthesis of kopsidasine, see: h) P. Magnus, A. H. Payne, L. Hobson, Tetrahedron Lett. 2000, 41, 2077-2081
58. i) P. Magnus, L. Gazzard, L. Hobson, A. H. Payne, T. J. Rainey, N. Westlund, V. Lynch, Tetrahedron 2002, 58, 3423-3443.
59. Part of this work was published as preliminary communications, see: a) Y. Oda, T. Sato, N. Chida, Org. Lett. 2012, 14, 950-953
60. b) K. Shirokane, T. Wada, M. Yoritate, R. Minamikawa, N. Takayama, T. Sato, N. Chida, Angew. Chem. Int. Ed. 2014, 53, 512-516
61. Angew. Chem. 2014, 126, 522-526.
62. a) P. C. Wailes, H. Weigold, J. Organomet. Chem. 1970, 24, 405-411
63. b) D. W. Hart, J. Schwartz, J. Am. Chem. Soc. 1974, 96, 8115-8116.
64. For chemoselective reductions of tertiary amides to aldehydes or their derivatives, see: a) S. Bower, K. A. Kreutzer, S. L. Buchwald, Angew. Chem. Int. Ed. Engl. 1996, 35, 1515-1516
65. Angew. Chem. 1996, 108, 1662-1664
66. b) J. M. White, A. R. Tunoori, G. I. Georg, J. Am. Chem. Soc. 2000, 122, 11995-11996
67. c) J. T. Spletstoser, J. M. White, A. R. Tunoori, G. I. Georg, J. Am. Chem. Soc. 2007, 129, 3408-3419
68. d) Y. Motoyama, M. Aoki, N. Takaoka, R. Aoto, H. Nagashima, Chem. Commun. 2009, 1574-1576
69. 3, see: e) Y. Zhao, V. Snieckus, Org. Lett. 2014, 16, 390-393.
70. For chemoselective reductions of secondary amides to imines, see: a) D. J. A. Schedler, A. G. Godfrey, B. Ganem, Tetrahedron Lett. 1993, 34, 5035-5038
71. b) D. J. A. Schedler, J. Li, B. Ganem, J. Org. Chem. 1996, 61, 4115-4119.
72. Ganem reported the chemoselective reductive cyanation of secondary amides with the Schwartz reagent and TMSCN, see: a) Q. Xia, B. Ganem, Org. Lett. 2001, 3, 485-487
73. b) Q. Xia, B. Ganem, Tetrahedron Lett. 2002, 43, 1597-1598
74. for a reductive phosphination of secondary amides, see: c) Y. Gao, Z. Huang, R. Zhuang, J. Xu, P. Zhang, G. Tang, Y. Zhao, Org. Lett. 2013, 15, 4214-4217.
75. For the reductive alkoxylation of cyanides with the Schwartz reagent, see; M. V. DeBenedetto, M. E. Green, S. Wan, J.-H. Park, P. E. Floreancig, Org. Lett. 2009, 11, 835-838.
76. 3 (1.3 equiv) and allyltributylstannane (3 equiv) at room temperature afforded 12a (21%), along with over-reduced byproduct I (32%). The Schwartz reagent played an important role, not only for the chemoselectivity, but also for the suppression of over-reduced byproduct I via chelated intermediate 6a. (EQUATION PRESENTED)
77. S. Nahm, S. M. Weinreb, Tetrahedron Lett. 1981, 22, 3815-3818.
78. Y. Kurosaki, K. Shirokane, T. Oishi, T. Sato, N. Chida, Org. Lett. 2012, 14, 2098-2101.
79. Our experimental results shown in Tables 2 and 4 were analyzed on the basis of the Mayr nucleophilicity index. Nucleophilic addition to N-me-thoxyamides via N-oxyiminium ions took place with nucleophiles that had a nucleophilicity parameter (N)≥5 (allyltributylstannane: N = 5.46, N-methylindole: N=5.75, silyl enol ethers: N=6.22, siloxyfuran: N = 7.22, silyl ketene acetals: N=9.00, 10.01). On the contrary, the reaction of the tertiary amide via the N-alkyliminium ion required nucleophiles with N≥7, except for allyltributylstannane. These results supported that the N-oxyiminium ions were more electrophilic than the N-alkyliminium ions. For the Mayr nucleophilicity index, see: a) H. Mayr, T. Bug, M. F. Gotta, N. Hering, B. Irrgang, B. Janker, B. Kempt, R. Loos, A. R. Ofial, G. Remennikov, H. Schimmel, J. Am. Chem. Soc. 2001, 123, 9500-9512
80. b) H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66-77
81. c) T. Tokuyasu, H. Mayr, Eur. J. Org. Chem. 2004, 2791-2796
82. d) S. Lakhdar, M. Westermaier, F. Terrier, R. Goumont, T. Boubaker, A. R. Ofial, H. Mayr, J. Org. Chem. 2006, 71, 9088-9095
83. e) J. Ammer, C. Nolte, H. Mayr, J. Am. Chem. Soc. 2012, 134, 13902-13911.