Catalytic, enantioselective intramolecular hydroamination of primary amines tethered to Di- and trisubstituted alkenes

Journal of Organic Chemistry

Volumn 76, Issue 24, 2011, Pages 10163-10172

  Chapurina, Yulia ^a,b   Ibrahim, Houssein ^a   Guillot, Régis ^c   Kolodziej, Emilie ^a,c   Collin, Jacqueline ^a,c   Trifonov, Alexander ^b   Schulz, Emmanuelle ^a,c   Hannedouche, Jérôme ^a,c  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b G A RAZUVAEV INSTITUTE OF ORGANOMETALLIC CHEMISTRY   (Russian Federation)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON-CARBON DOUBLE BONDS; CHIRAL COMPLEXES; CHIRAL ENVIRONMENT; EFFICIENT CATALYSTS; ENANTIOSELECTIVE; FINE TUNING; HETEROLEPTIC COMPLEXES; HIGH REACTION TEMPERATURES; HYDROAMINATIONS; IN-SITU; INTRAMOLECULAR HYDROAMINATION; PRIMARY AMINES; QUATERNARY CENTERS; STERICALLY DEMANDING; TRISUBSTITUTED ALKENES; YTTRIUM COMPLEXES;

AMINES; ENANTIOSELECTIVITY; OLEFINS; YTTRIUM;

CYCLIZATION;

ALKENE DERIVATIVE; AMINE; CARBON; DIAMINE DERIVATIVE; YTTRIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; CYCLIZATION; ENANTIOSELECTIVITY; HYDROAMINATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84055193817     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202009q     Document Type: Article

References (64)

1. (a) Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
2. (b) Brunet, J. J.; Neibecker, D. In Catalytic Heterofunctionalization from Hydroamination to Hydrozirconation; Togni, A., Grutzmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001; pp 91-141.
3. (c) Nobis, M.; Driessen-Holscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983-3985.
4. (d) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104-114.
5. (e) Muller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795-3892.
6. (a) Roesky, P. W.; Muller, T. E. Angew. Chem., Int. Ed. 2003, 42, 2708-2710.
7. (b) Hultzsch, K. C. Org. Biomol. Chem. 2005, 3, 1819-1824.
8. (c) Hultzsch, K. C. Adv. Synth. Catal. 2005, 347, 367-391.
9. (d) Aillaud, I.; Collin, J.; Hannedouche, J.; Schulz, E. Dalton Trans. 2007, 5105-5118.
10. (e) Chemler, S. R. Org. Biomol. Chem. 2009, 7, 3009-3019.
11. (f) Zi, G. Dalton Trans. 2009, 9101-9109.
12. (a) Dorta, R.; Egli, P.; Zurcher, F.; Togni, A. J. Am. Chem. Soc. 1997, 119, 10857-10858.
13. (b) Lober, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366-4367.
14. (c) Brunet, J. J.; Cadena, M.; Chu, N. C.; Diallo, O.; Jacob, K.; Mothes, E. Organometallics 2004, 23, 1264-1268.
15. (d) Johns, A. M.; Utsunomiya, M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 1828-1839.
16. (e) Patil, N. T.; Lutete, L. M.; Wu, H.; Pahadi, N. K.; Gridnev, I. D.; Yamamoto, Y. J. Org. Chem. 2006, 71, 4270-4279.
17. (f) LaLonde, R. L.; Sherry, B. D.; Kang, E. J.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2452-2453.
18. (g) Bender, C. F.; Hudson, W. B.; Widenhoefer, R. A. Organometallics 2008, 27, 2356-2358.
19. (h) Liu, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 12220-12221.
20. (i) Hesp, K. D.; Stradiotto, M. Org. Lett. 2009, 11, 1449-1452.
21. (j) Shen, X.; Buchwald, S. L. Angew. Chem., Int. Ed. 2010, 49, 564-567.
22. (a) Gribkov, D. V.; Hultzsch, K. C. Angew. Chem., Int. Ed. 2004, 43, 5542-5546.
23. (b) Knight, P. D.; Munslow, I.; O'Shaughnessy, P. N.; Scott, P. Chem. Commun. 2004, 894-895.
24. (c) Kim, H.; Lee, P. H.; Livinghouse, T. Chem. Commun. 2005, 5205-5207.
25. (d) Watson, D. A.; Chiu, M.; Bergman, R. G. Organometallics 2006, 25, 4731-4733.
26. (e) Wood, M. C.; Leitch, D. C.; Yeung, C. S.; Kozak, J. A.; Schafer, L. L. Angew. Chem., Int. Ed. 2007, 46, 354-358.
27. (f) Manna, K.; Xu, S.; Sadow, A. D. Angew. Chem., Int. Ed. 2011, 50, 1865-1868.
28. Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
29. (a) Gagne, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108-4109.
30. (b) Gagne, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716-1718.
31. (c) Gagne, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275-294.
32. (d) Gagne, M. R; Brard, L.; Conticello, V. P.; Giardello, M. A.; Stern, C. L.; Marks, T. J. Organometallics 1992, 11, 2003-2005.
33. (a) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770-3772.
34. (b) Ryu, J.-S.; Li, G Y.; Marks, T.J. J. Am. Chem. Soc. 2003, 125, 12584-12605.
35. (c) Gribkov, D. V.; Hultzsch, K. C.; Hampel, F. J. Am. Chem. Soc. 2006, 128, 3748-3759.
36. (d) Reznichenko, A. L.; Nguyen, H. N.; Hultzsch, K C. Angew. Chem., Int. Ed. 2010, 49, 8984-8987.
37. (a) Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 1737-1739.
38. Reznichenko, A L.; Hultzsch, K. C. Organometallics 2010, 29, 24-27.
39. Ryu, J.-S.; Marks, T. J.; McDonald, F. E. Org. Lett. 2001, 3, 3091-3094.
40. Ryu, J.-S.; Marks, T. J.; McDonald, F. E.J. Org. Chem. 2004, 69, 1038-1052.
41. Leitch, D. C.; Payne, P. R; Dunbar, C. R; Schafer, L. L. J. Am. Chem. Soc. 2009, 131, 18246-18247.
42. (a) Molander, G A; Dowdy, E. D. J. Org. Chem. 1998, 63, 8983-8988.
43. (b) Molander, G A.; Dowdy, E. D. J. Org. Chem. 1999, 64, 6515-6517.
44. Hegedus, L. S.; Allen, G F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 100, 5800-5807.
45. (a) Kim, Y. K; Livinghouse, T.; Bercaw, J. E. Tetrahedron Lett. 2001, 42, 2933-2935.
46. (b) Kim, H; Lee, P. H; Livinghouse, T. Chem. Commun. 2005, 5205-5207.
47. (c) Kim, H; Kim, Y. K.; Shim, J. H; Kim, M.; Han, M.; Livinghouse, T.; Lee, P. H. Adv. Synth. Catal. 2006, 348, 2609-2618.
48. (d) Liu, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 1570-1571.
49. (e) Cho, J.; Hollis, T. K.; Helgert, T. R; Valente, E. J. Chem. Commun. 2008, 40, 5001-5003.
50. (f) Crimmin, M. R; Arrowsmith, M.; Barrett, A. G M.; Casely, I. J.; Hill, M. S.; Procopiou, P. A. J. Am. Chem. Soc. 2009, 131, 9670-9685.
51. (g) Arrowsmith, M.; Hill, M. S.; Kociok-Kohn, G Organometallics 2009, 28, 1730-1738.
52. (h) Kitahara, H.; Sakurai, H. Chem. Lett. 2010, 39, 46-48.
53. Chapurina, Y.; Hannedouche, J.; Collin, J.; Guillot, R; Schulz, E.; Trifonov, A. Chem. Commun. 2010, 46, 6918-6920.
54. Wang, B.; Wang, D.; Cui, D.; Gao, W.; Tang, T.; Chen, X.; Jing, X. Organometallics 2007, 26, 3167-3172.
55. (a) Hannedouche, J.; Allaud, I.; Collin, J.; Schulz, E.; Trifonov, A. Chem. Commun. 2008, 3552-3554.
56. (b) Allaud, I.; Lyubov, D.; Collin, J.; Guillot, R; Hannedouche, J.; Schulz, E.; Trifonov, A. Organometallics 2008, 27, 5929-5936.
57. (c) Hannedouche, J.; Collin, J.; Trifonov, A; Schulz, E. J. Organomet. Chem. 2011, 69, 255-262.
58. Allaud, I.; Collin, J.; Duhayon, C.; Guillot, R; Lyubov, D.; Schulz, E.; Trifonov, A Chem.-Eur. J. 2008, 14, 2189-2200.
59. Arrowsmith, M.; Crimmin, M. R; Barett, A G; Hill, M. S.; Kociok-Kohn, G; Procopiou, A. P. Organometallics 2011, 30, 1493-1506.
60. Allaud, I.; Wright, K.; Collin, J.; Schulz, E.; Mazaleyrat, J.-P. Tetrahedron: Asymmetry 2008, 19, 82-92.
61. Riegert, D.; Collin, J.; Meddour, A.; Schulz, E.; Trifonov, A. J. Org. Chem. 2006, 71, 2514-2517.
62. Tamaru, Y.; Hojo, M.; Higashimura, H; Yoshida, Z.-I. J. Am. Chem. Soc. 1988, 110, 3994-4002.
63. Kondo, T.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 2002, 124, 186-187.
64. Zhang, Z.; Bender, C. F.; Widenhoefer, R A. J. Am. Chem. Soc. 2007, 129, 14148-14149.