Synthesis of β-Boryl-α-Aminosilanes by Copper-Catalyzed Aminoboration of Vinylsilanes

Angewandte Chemie - International Edition

Volumn 55, Issue 46, 2016, Pages 14400-14404

  Kato, Kodai ^a   Hirano, Koji ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

boron; copper; electrophilic amination; synthetic methods; aminosilanes

Indexed keywords

AMINATION; AMINES; BORON; COPPER; COPPER COMPOUNDS;

AMINOSILANES; ASYMMETRIC CATALYSIS; COPPER CATALYZED; DIASTEREO-SELECTIVITY; ELECTROPHILIC AMINATION; MEDICINAL CHEMISTRY; REGIO-SELECTIVE; SYNTHETIC METHODS;

CATALYSIS;

EID: 84994030153     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201608139     Document Type: Article

References (83)

1. T. Hiyama, T. Kusamoto in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, Chap. 3.12;
2. The Chemistry of Organosilicon Compounds (Eds.: Z. Rappoport, Y. Apeloig), Wiley, Chichester, 1998.
3. J. Kim, S. M. Sieburth, Bioorg. Med. Chem. Lett. 2004, 14, 2853;
4. J. Kim, G. Hewitt, P. Carroll, S. M. Sieburth, J. Org. Chem. 2005, 70, 5781;
5. L. Nielsen, K. B. Lindsay, J. Faber, N. C. Nielsen, T. Skrydstrup, J. Org. Chem. 2007, 72, 10035;
6. L. Nielsen, T. Skrydstrup, J. Am. Chem. Soc. 2008, 130, 13145;
7. N. A. Meanwell, J. Med. Chem. 2011, 54, 2529;
8. A. K. Franz, S. O. Wilson, J. Med. Chem. 2012, 55, 388.
9. D. M. Ballweg, R. C. Miller, D. J. Gray, K. A. Scheidt, Org. Lett. 2005, 7, 1403;
10. D. Hernández, K. B. Lindsay, L. Nielsen, T. Mittag, K. Bjerglund, S. Friis, R. Mose, T. Skrydstrup, J. Org. Chem. 2010, 75, 3283;
11. D. Hernández, L. Nielsen, K. B. Lindsay, M. A. Lopez-Garcia, K. Bjerglund, T. Skrydstrup, Org. Lett. 2010, 12, 3528;
12. D. Hernández, R. Mose, T. Skrydstrup, Org. Lett. 2010, 12, 732;
13. Y. Bao, S. Singh, H. Q. Duong, C. Cao, S. M. Sieburth, Org. Lett. 2011, 13, 1787.
14. A. Hensel, K. Nagura, L. B. Delvos, M. Oestreich, Angew. Chem. Int. Ed. 2014, 53, 4964;
15. Angew. Chem. 2014, 126, 5064;
16. T. Mita, M. Sugawara, K. Saito, Y. Sato, Org. Lett. 2014, 16, 3028;
17. C. Zhao, C. Jiang, J. Wang, C. Wu, Q.-W. Zhang, W. He, Asian J. Org. Chem. 2014, 3, 851.
18. N. Niljianskul, S. Zhu, S. L. Buchwald, Angew. Chem. Int. Ed. 2015, 54, 1638;
19. Angew. Chem. 2015, 127, 1658; also see:
20. S. Zhu, N. Niljianskul, S. L. Buchwald, J. Am. Chem. Soc. 2013, 135, 15746;
21. S. Zhu, S. L. Buchwald, J. Am. Chem. Soc. 2014, 136, 15913;
22. S.-L. Shi, S. L. Buchwald, Nat. Chem. 2015, 7, 38;
23. Y. Yang, S.-L. Shi, D. Niu, P. Liu, S. L. Buchwald, Science 2015, 349, 62.
24. For selected examples of electrophilic amination reactions with the hydroxylamine, see:
25. K. Narasaka, M. Kitamura, Eur. J. Org. Chem. 2005, 4505;
26. A. M. Berman, J. S. Johnson, J. Am. Chem. Soc. 2004, 126, 5680;
27. M. J. Campbell, J. S. Johnson, Org. Lett. 2007, 9, 1521;
28. S. Liu, L. S. Liebeskind, J. Am. Chem. Soc. 2008, 130, 6918;
29. R. P. Rucker, A. M. Whittaker, H. Dang, G. Lalic, J. Am. Chem. Soc. 2012, 134, 6571;
30. S. N. Mlynarski, A. S. Karns, J. P. Morken, J. Am. Chem. Soc. 2012, 134, 16449;
31. C. Zhu, G. Li, D. H. Ess, J. R. Falck, L. Kürti, J. Am. Chem. Soc. 2012, 134, 18253;
32. Z. Dong, G. Dong, J. Am. Chem. Soc. 2013, 135, 18350;
33. S. L. McDonald, Q. Wang, Angew. Chem. Int. Ed. 2014, 53, 1867;
34. Angew. Chem. 2014, 126, 1898;
35. M. Shang, S.-H. Zeng, S.-Z. Sun, H.-X. Dai, J.-Q. Yu, Org. Lett. 2013, 15, 5286;
36. P. Patel, S. Chang, Org. Lett. 2014, 16, 3328;
37. J. He, T, Shigenari, J.-Q. Yu, Angew. Chem. Int. Ed. 2015, 54, 6545;
38. Angew. Chem. 2015, 127, 6645.
39. For additional approaches to the α-aminosilane, see:
40. C. Barberis, N. Voyer, Tetrahedron Lett. 1998, 39, 6807;
41. S. M. Sieburth, H. K. O'Hare, J. Xu, Y. Chen, G. Liu, Org. Lett. 2003, 5, 1859;
42. S. M. Sieburth, G. Liu, Org. Lett. 2003, 5, 4677.
43. N. Matsuda, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2013, 135, 4934;
44. R. Sakae, N. Matsuda, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2014, 16, 1228;
45. R. Sakae, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2015, 54, 613;
46. Angew. Chem. 2015, 127, 623;
47. R. Sakae, K. Hirano, M. Miura, J. Am. Chem. Soc. 2015, 137, 6460; also see:
48. T. Kawano, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2010, 132, 6900;
49. N. Matsuda, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2012, 51, 3642;
50. Angew. Chem. 2012, 124, 3702;
51. N. Matsuda, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2012, 51, 11827;
52. Angew. Chem. 2012, 124, 11997;
53. Y. Miki, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2013, 52, 10830;
54. Angew. Chem. 2013, 125, 11030;
55. D. Nishikawa, K. Hirano, M. Miura, J. Am. Chem. Soc. 2015, 137, 15620.
56. D. S. Laitar, P. Müller, J. P. Sadighi, J. Am. Chem. Soc. 2005, 127, 17196.
57. D. S. Laitar, E. Y. Tsui, J. P. Sadighi, Organometallics 2006, 25, 2405.
58. Recent computational studies suggest the SN2-type oxidative addition/reductive elimination sequence in the C−N forming step; S. Tobisch, Chem. Eur. J. 2016, 22, 8290.
59. H. Ito, Y. Kosaka, K. Nonoyama, Y. Sasaki, M. Sawamura, Angew. Chem. Int. Ed. 2008, 47, 7424;
60. Angew. Chem. 2008, 120, 7534;
61. H. Ito, T. Toyoda, M. Sawamura, J. Am. Chem. Soc. 2010, 132, 5990;
62. K. Kubota, E. Yamamoto, H. Ito, Adv. Synth. Catal. 2013, 355, 3527;
63. F. Meng, H. Jang, A. H. Hoveyda, Chem. Eur. J. 2013, 19, 3204;
64. H. Yoshida, I. Kageyuki, K. Takaki, Org. Lett. 2013, 15, 952.
65. The syn stereochemistry can be eroded in the C−N forming step. For relevant observations of alkylcopper species, see:
66. C. Zhong, S. Kunii, Y. Kosaka, M. Sawamura, H. Ito, J. Am. Chem. Soc. 2010, 132, 11440;
67. K. M. Logan, K. B. Smith, M. K. Brown, Angew. Chem. Int. Ed. 2015, 54, 5228;
68. Angew. Chem. 2015, 127, 5317;
69. K. Semba, K. Ariyama, H. Zheng, R. Kameyama, S. Sakaki, Y. Nakao, Angew. Chem. Int. Ed. 2016, 55, 6275;
70. Angew. Chem. 2016, 128, 6383. Additionally, the syn/anti diastereoselectivity was somewhat dependent on the external ligand. See the Supporting Information for more detailed optimization studies.
71. The syn stereochemistry of 3 ba was determined by X-ray analysis after the derivatization into the corresponding ester (see the Supporting Information for details). The relative stereochemistry of other products from alkyl-substituted vinylsilanes was tentatively assigned by analogy.
72. The β-boryl-α-aminosilanes bearing the Ph group on Si were somewhat unstable for the silica gel column chromatography and thus isolated after the oxidation.
73. See the Supporting Information for details.
74. L. Dang, H. Zhao, Z. Lin, T. B. Marder, Organometallics 2007, 26, 2824;
75. L. Deng, Z. Lin, T. B. Marder, Organometallics 2008, 27, 4443.
76. M. Noack, R. Göttlich, Chem. Commun. 2002, 536; also see:
77. T. Tsuritani, H. Shinokubo, K. Oshima, Org. Lett. 2001, 3, 2709;
78. B. N. Hemric, K. Shen, Q. Wang, J. Am. Chem. Soc. 2016, 138, 5813.
79. H. Noguchi, K. Hojo, M. Suginome, J. Am. Chem. Soc. 2007, 129, 758;
80. J. L. Wood, L. D. Marciasini, M. Vaultier, M. Pucheault, Synlett 2014, 25, 551.
81. J. Raushel, D. L. Sandrock, K. V. Josyula, D. Pakyz, G. A. Molander, J. Org. Chem. 2011, 76, 2762.
82. Unfortunately, the β-aminoborane 3 fa could not be directly applied to the Suzuki–Miyaura coupling under the present conditions. This is probably because the intermolecular tight chelation of N to B in 3 fa interferes with the effective transmetalation between B and Pd.
83. See the Supporting Information for optimization studies on asymmetric catalysis.