Enantioselective C-H amination using cationic ruthenium(II)-pybox catalysts

Angewandte Chemie - International Edition

Volumn 47, Issue 36, 2008, Pages 6825-6828

  Milczek, Erika ^a   Boudet, Nadège ^a   Blakey, Simon ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

Amination; Asymmetric catalysis; C H activation; Ruthenium

Indexed keywords

AMINATION; AMINES; CATALYSIS; DYES; ENANTIOSELECTIVITY; RUTHENIUM;

AMINATION REACTIONS; ASYMMETRIC CATALYSIS; BENZYLIC; C-H ACTIVATION; C-H BONDS; ENANTIOSELECTIVE; PYBOX COMPLEXES; STEREOCONTROL; TERT-BUTOXYCARBONYL;

RUTHENIUM COMPOUNDS;

EID: 53249096011     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801445     Document Type: Article

References (38)

1. a) R. Breslow, S. H. Gellman, J. Chem. Soc. Chem. Commun. 1982, 1400;
2. b) R. Breslow, S. H. Gellman, J. Am. Chem. Soc. 1983, 105, 6728.
3. a) C. G. Espino, J. Du Bois, Angew. Chem. 2001, 113, 618;
4. Angew. Chem. Int. Ed. 2001, 40, 598;
5. b) C. G. Espino, P. M. Wehn, J. Chow, J. Du Bois, J. Am. Chem. Soc. 2001, 123, 6935;
6. c) C. G. Espino, K. W. Fiori, M. Kim, J. Du Bois, J. Am. Chem. Soc. 2004, 126, 15378;
7. d) M. Kim, J. V. Mulcahy, C. G. Espino, J. Du Bois, Org. Lett. 2006, 8, 1073;
8. e) K. W. Fiori, J. Du Bois, J. Am. Chem. Soc. 2007, 129, 562.
9. a) S. M. Au, S. B. Zhang, W. H. Fung, W. Y. Yu, C. M. Che, K. K. Cheung, Chem. Commun. 1998, 2677;
10. b) S. M. Au, J. S. Huang, W. Y. Yu, W. H. Fung, C. M. Che, J. Am. Chem. Soc. 1999, 121, 9120;
11. c) X.-G. Zhou, X.-Q. Yu, J.-S. Huang, C.-M. Che, Chem. Commun. 1999, 2377;
12. d) S. M. Au, J. S. Huang, C. M. Che, W. Y. Yu, J. Org. Chem. 2000, 65, 7858;
13. e) X. Q. Yu, J. S. Huang, X. G. Zhou, C. M. Che, Org. Lett. 2000, 2, 2233;
14. f) J.-L. Liang, S.-X. Yuan, J.-S. Huang, W.-Y. Yu, C.-M. Che, Angew. Chem. 2002, 114, 3615;
15. Angew. Chem. Int. Ed. 2002, 41, 3465;
16. g) S. K. Y. Leung, W. M. Tsui, J. S. Huang, C. M. Che, J. L. Liang, N. Y. Zhu, J. Am. Chem. Soc. 2005, 127, 16629.
17. a) Y. Cui, C. He, Angew. Chem. 2004, 116, 4306;
18. Angew. Chem. Int. Ed. 2004, 43, 4210;
19. b) Z. Li, D. A. Capretto, R. Rahaman, C. He, Angew. Chem. 2007, 119, 5276;
20. Angew. Chem. Int. Ed. 2007, 46, 5184.
21. H. Lebel, K. Huard, S. Lectard, J. Am. Chem. Soc. 2005, 127, 14198.
22. H. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861.
23. a) M. Yamawaki, H. Tsutsui, S. Kitagaki, M. Anada, S. Hashimoto, Tetrahedron Lett. 2002, 43, 9561;
24. b) C. Fruit, P. Muller, Helv. Chem. Acta 2004, 87, 1607;
25. c) R. P. Reddy, H. M. L. Davies, Org. Lett. 2006, 8, 5013;
26. for other catalysts see Ref. [2] and d) Y. Kohmura, T. Katsuki, Tetrahedron Lett. 2001, 42, 3339;
27. e) K. Omura, M. Murakami, T. Uchida, R. Irie, T. Katsuki, Chem. Lett. 2003, 32, 354.
28. a) C. Liang, F. Robert-Peillard, C. Fruit, P. Mueller, R. H. Dodd, P. Dauban, Angew. Chem. 2006, 118, 4757;
29. Angew. Chem. Int. Ed. 2006, 45, 4641;
30. b) C. Liang, F. Collet, F. Robert-Peillard, P. Mueller, R. H. Dodd, P. Dauban, J. Am. Chem. Soc. 2008, 130, 343.
31. H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223.
32. At the time of this investigation, the best reported results for the enantioselective cyclization of this substrate were 84% ee, 48% yield; see Ref. [3].
33. J. L. Liang, S. X. Yuan, J. S. Huang, C. M. Che, J. Org. Chem. 2004, 69, 3610.
34. K. Guthikonda, P. M. When, B. J. Caliando, J. Du Bois, Tetrahedron 2006, 62, 11331.
35. For a recent review on the use of olefins as ligands in transition-metal-catalyzed reactions, see: J. B. Johnson, T. Rovis, Angew. Chem. 2008, 120, 852;
36. Angew. Chem. Int. Ed. 2008, 47, 840.
37. trans-Cyclooctene has been used as a ligand in an analogous but less sterically encumbered ruthenium(II)-pybox complex: H. Nishiyama, T. Naitoh, Y. Motoyama, K. Aoki, Chem. Eur. J. 1999, 5, 3509.
38. For a similar model in the context of Ru-catalyzed cyclopropanation, see: H. Nishiyama, Y, Itoh, Y. Sugiwara, H. Matsumoto, K. Aoki, K. Itoh, Bull. Chem. Soc. Jpn. 1995, 68, 1247.