Design of modified amine transfer reagents allows the synthesis of α-chiral secondary amines via CuH-catalyzed hydroamination

Journal of the American Chemical Society

Volumn 137, Issue 30, 2015, Pages 9716-9721

  Niu, Dawen ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; CATALYSIS; HYDROCARBONS;

AMINO ACID ESTERS; CATALYZED SYNTHESIS; CURRENT TECHNOLOGY; DIRECT REACTIONS; HIGH-EFFICIENCY; HYDROAMINATIONS; MODIFIED AMINES; SECONDARY AMINES;

CHEMICAL REACTIONS;

AMINE; COPPER; ALKENE; HYDROGEN;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; HYDROAMINATION; SYNTHESIS; CATALYSIS; CHEMISTRY;

ALKENES; AMINATION; AMINES; CATALYSIS; COPPER; HYDROGEN; MOLECULAR STRUCTURE;

EID: 84938820736     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b05446     Document Type: Article

References (60)

1. Nugent, T. C., Ed. Chiral Amine Synthesis: Methods, Developments and Applications; Wiley-VCH: Weinheim, Germany, 2010.
2. Turner, N. J.; Carr, R. Biocatalytic Routes to Nonracemic Chiral Amines. In Biocatalysis in the Pharmaceutical and Biotechnology Industries; Patel, R. N., Ed.; CRC Press LLC: Boca Raton, FL, 2006; pp 743-755.
3. Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600 10.1021/cr900382t
4. Nugent, T. C.; El-Shazly, M. Adv. Synth. Catal. 2010, 352, 753 10.1002/adsc.200900719
5. Xie, J.; Zhu, S.; Zhou, Q. Chem. Rev. 2011, 111, 1713 10.1021/cr100218m
6. Tufvesson, P.; Lima-Ramos, J.; Jensen, J. S.; Al-Haque, N.; Neto, W.; Woodley, J. M. Biotechnol. Bioeng. 2011, 108, 1479 10.1002/bit.23154
7. Gopalaiah, K. Chem. Rev. 2013, 113, 3248 10.1021/cr300236r
8. Feng, X.; Du, H. Tetrahedron Lett. 2014, 55, 6959 10.1016/j.tetlet.2014.10.138
9. Bloch, R. Chem. Rev. 1998, 98, 1407 10.1021/cr940474e
10. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069 10.1021/cr980414z
11. Friestad, G. K.; Mathies, A. K. Tetrahedron 2007, 63, 2541 10.1016/j.tet.2006.11.076
12. Yamada, K.; Tomioka, K. Chem. Rev. 2008, 108, 2874 10.1021/cr078370u
13. Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626 10.1021/cr100204f
14. Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2011, 111, 7774 10.1021/cr1004474
15. Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2014, 114, 9047 10.1021/cr5001496
16. Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689 10.1021/cr970343o
17. Helmchen, G. Iridium-Catalyzed Asymmetric Allylic Substitutions. In Iridium Complexes in Organic Synthesis; Oro, L. A.; Claver, C., Eds.; Wiley-VCH: Weinheim, Germany, 2009; pp 211-250.
18. Hartwig, J. F.; Stanley, L. M. Acc. Chem. Res. 2010, 43, 1461 10.1021/ar100047x
19. Liu, W.-B.; Xia, J.-B.; You, S.-L. Top. Organomet. Chem. 2012, 38, 155 10.1007/3418-2011-10
20. Tosatti, P.; Nelson, A.; Marsden, S. P. Org. Biomol. Chem. 2012, 10, 3147 10.1039/c2ob07086c
21. Roizen, J. L.; Harvey, M. E.; Du Bois, J. Acc. Chem. Res. 2012, 45, 911 10.1021/ar200318q
22. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417 10.1038/nature06485
23. Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905 10.1021/cr020043t
24. Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675 10.1021/cr960433d
25. Hartwig, J. F. Pure Appl. Chem. 2004, 76, 507 10.1351/pac200476030507
26. Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673 10.1021/ar040051r
27. Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368 10.1002/anie.200300616
28. Hultzsch, K. C. Org. Biomol. Chem. 2005, 3, 1819 10.1039/b418521h
29. Muller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795 10.1021/cr0306788
30. Hultzsch, K. C. Adv. Synth. Catal. 2005, 347, 367 10.1002/adsc.200404261
31. Huang, L.; Arndt, M.; Gooen, K.; Heydt, H.; Gooen, L. J. Chem. Rev. 2015, 115, 2596 10.1021/cr300389u
32. Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473 10.1021/ja992366l
33. Hughes, G.; Kimura, M.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11253 10.1021/ja0351692
34. Rainka, M. P.; Aye, Y.; Buchwald, S. L. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5821 10.1073/pnas.0307764101
35. Berman, A. M.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 5680 10.1021/ja049474e
36. Berman, A. M.; Johnson, J. S. J. Org. Chem. 2006, 71, 219 10.1021/jo051999h
37. Campbell, M. J.; Johnson, J. S. Org. Lett. 2007, 9, 1521 10.1021/ol0702829
38. Rucker, R. P.; Whittaker, A. M.; Dang, H.; Lalic, G. Angew. Chem., Int. Ed. 2012, 51, 3953 10.1002/anie.201200480
39. Yan, X.; Yang, X.; Xi, C. Catal. Sci. Technol. 2014, 4, 4169 10.1039/C4CY00773E
40. Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947 10.1021/cr00098a014
41. Barker, T. J.; Jarvo, E. R. Synthesis 2011, 24, 3954 10.1055/s-0031-1289581
42. Zhu, S.; Niljianskul, N.; Buchwald, S. L. J. Am. Chem. Soc. 2013, 135, 15746 10.1021/ja4092819
43. Zhu, S.; Buchwald, S. L. J. Am. Chem. Soc. 2014, 136, 15913 10.1021/ja509786v
44. Niljianskul, N.; Zhu, S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2015, 54, 1638 10.1002/anie.201410326
45. Shi, S.; Buchwald, S. L. Nat. Chem. 2015, 7, 38 10.1038/nchem.2131
46. Miki, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 10830 10.1002/anie.201304365
47. Miki, Y.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2014, 16, 1498 10.1021/ol5003219
48. Yotphan, S.; Beukeaw, D.; Reutrakul, V. Tetrahedron 2013, 69, 6627 10.1016/j.tet.2013.05.127
49. McDonald, S. L.; Wang, Q. Angew. Chem., Int. Ed. 2014, 53, 1867 10.1002/anie.201308890
50. Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2011, 13, 2860 10.1021/ol200855t
51. Ascic, E.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 4666-4669 10.1021/jacs.5b02316
52. 3 is used as a secondary ligand due to the observed beneficial effects it has on CuH-catalyzed reactions. This concept was developed by Lipshutz: Lipshutz, B. H.; Noson, K.; Chrisman, W.; Lower, A. J. Am. Chem. Soc. 2003, 125, 8779 10.1021/ja021391f
53. Grigg, R. D.; Van Hoveln, R.; Schomaker, J. M. J. Am. Chem. Soc. 2012, 134, 16131 10.1021/ja306446m
54. Van Hoveln, R. J.; Schmid, S. C.; Schomaker, J. M. Org. Biomol. Chem. 2014, 12, 7655 10.1039/C4OB01294A
55. Smithen, D. A.; Mathews, C. J.; Tomkinson, N. C. O. Org. Biomol. Chem. 2012, 10, 3756 10.1039/c2ob25293g
56. Tokuyama, H.; Kuboyama, T.; Fukuyama, T. Org. Synth. 2003, 80, 207 10.15227/orgsyn.080.0207
57. Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J. J. Org. Chem. 1990, 55, 1981 10.1021/jo00294a005
58. Fukuzumi, T.; Bode, J. W. J. Am. Chem. Soc. 2009, 131, 3864 10.1021/ja900601c
59. Sun, H.; Martin, C.; Kesselring, D.; Keller, R.; Moeller, K. D. J. Am. Chem. Soc. 2006, 128, 13761 10.1021/ja064737l
60. Molander, G. A.; Brown, A. R. J. Org. Chem. 2006, 71, 9681 10.1021/jo0617013