Utility of the iridium complex of the pybox ligand in regio- and enantioselective allylic substitution

Organic Letters

Volumn 6, Issue 24, 2004, Pages 4631-4634

  Miyabe, Hideto ^a   Matsumura, Akira ^a   Moriyama, Katsuhiko ^a   Takemoto, Yoshiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINE; ANILINE; ETHER DERIVATIVE; HYDROXYLAMINE; IRIDIUM COMPLEX; LIGAND; OXIME; OXIME DERIVATIVE;

ALLYLATION; AMINATION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 10044284259     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047915t     Document Type: Article

References (41)

1. For reviews, see: (a) Trost B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921. (b) Trost, B. M.; Lee, C. B. In Catalytic Asymmetric Synthesis II; Ojima, I. Ed.; Wiley-VCH: Weinheim, Germany, 2000; pp 593-650. (c) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp. 833-884. (d) Trost B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 2921.
2. For reviews, see: (a) Trost B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921. (b) Trost, B. M.; Lee, C. B. In Catalytic Asymmetric Synthesis II; Ojima, I. Ed.; Wiley-VCH: Weinheim, Germany, 2000; pp 593-650. (c) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp. 833-884. (d) Trost B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 2921.
3. For reviews, see: (a) Trost B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921. (b) Trost, B. M.; Lee, C. B. In Catalytic Asymmetric Synthesis II; Ojima, I. Ed.; Wiley-VCH: Weinheim, Germany, 2000; pp 593-650. (c) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp. 833-884. (d) Trost B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 2921.
4. For reviews, see: (a) Trost B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921. (b) Trost, B. M.; Lee, C. B. In Catalytic Asymmetric Synthesis II; Ojima, I. Ed.; Wiley-VCH: Weinheim, Germany, 2000; pp 593-650. (c) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp. 833-884. (d) Trost B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 2921.
5. For recent reviews, see: (a) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2004, 103, 3263. (b) Desimoni, G.; Faita, G.; Quadrelli, P. Chem. Rev. 2003, 103, 3119. (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
6. For recent reviews, see: (a) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2004, 103, 3263. (b) Desimoni, G.; Faita, G.; Quadrelli, P. Chem. Rev. 2003, 103, 3119. (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
7. For recent reviews, see: (a) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2004, 103, 3263. (b) Desimoni, G.; Faita, G.; Quadrelli, P. Chem. Rev. 2003, 103, 3119. (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
8. (a) Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
9. (b) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Ruegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265.
10. (c) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482.
11. (a) Bourguignon, J.; Bremberg, U.; Dupas, G.; Hallman, K.; Hagberg, L.; Hortala, L.; Levacher, V.; Lutsenko, S.; Macedo, E.; Moberg, C.; Quéguiner, C.; Rahm, F. Tetrahedron 2003, 59, 9583.
12. (b) Chelucci, G.; Deriu, S.; Pinna, G. A.; Saba, A.; Valenti, R. Tetrahedron: Asymmetry 1999, 10, 3803.
13. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846.
14. Recently, the iridium-idane-pybox catalyst was used in a reductive aldol reaction. See: Zhao, C-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
15. (a) Takeuchi, R.; Ue, N.; Tanabe, K.; Yamashita, K.; Shiga, N. J. Am. Chem. Soc. 2001, 123, 9525.
16. (b) Takeuchi R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647.
17. For a review, see: (c) Takeuchi, R. Synlett 2002, 1954.
18. For some examples, see: (a) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681. (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4546. (c) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761. (d) Trost, B. M.; Tsui, H.-C.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 3534. (e) You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471.
19. For some examples, see: (a) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681. (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4546. (c) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761. (d) Trost, B. M.; Tsui, H.-C.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 3534. (e) You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471.
20. For some examples, see: (a) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681. (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4546. (c) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761. (d) Trost, B. M.; Tsui, H.-C.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 3534. (e) You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471.
21. For some examples, see: (a) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681. (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4546. (c) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761. (d) Trost, B. M.; Tsui, H.-C.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 3534. (e) You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471.
22. For some examples, see: (a) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681. (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4546. (c) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761. (d) Trost, B. M.; Tsui, H.-C.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 3534. (e) You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471.
23. For some related examples, see: (a) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426. (b) Alexakis, A.: Polet, D. Org. Lett. 2004, 6, 3529. (c) Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794. (d) Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797. (e) Lipowsky, G.; Helmchen G. Chem. Commun. 2004, 116. (f) Fisher, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1629. (g) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426. (h) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (i) Fuji, K.; Kinoshita, N.; Tanaka K.; Kawabata, T. Chem. Commun. 1999, 2289. (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
24. For some related examples, see: (a) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426. (b) Alexakis, A.: Polet, D. Org. Lett. 2004, 6, 3529. (c) Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794. (d) Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797. (e) Lipowsky, G.; Helmchen G. Chem. Commun. 2004, 116. (f) Fisher, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1629. (g) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426. (h) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (i) Fuji, K.; Kinoshita, N.; Tanaka K.; Kawabata, T. Chem. Commun. 1999, 2289. (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
25. For some related examples, see: (a) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426. (b) Alexakis, A.: Polet, D. Org. Lett. 2004, 6, 3529. (c) Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794. (d) Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797. (e) Lipowsky, G.; Helmchen G. Chem. Commun. 2004, 116. (f) Fisher, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1629. (g) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426. (h) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (i) Fuji, K.; Kinoshita, N.; Tanaka K.; Kawabata, T. Chem. Commun. 1999, 2289. (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
26. For some related examples, see: (a) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426. (b) Alexakis, A.: Polet, D. Org. Lett. 2004, 6, 3529. (c) Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794. (d) Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797. (e) Lipowsky, G.; Helmchen G. Chem. Commun. 2004, 116. (f) Fisher, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1629. (g) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426. (h) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (i) Fuji, K.; Kinoshita, N.; Tanaka K.; Kawabata, T. Chem. Commun. 1999, 2289. (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
27. For some related examples, see: (a) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426. (b) Alexakis, A.: Polet, D. Org. Lett. 2004, 6, 3529. (c) Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794. (d) Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797. (e) Lipowsky, G.; Helmchen G. Chem. Commun. 2004, 116. (f) Fisher, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1629. (g) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426. (h) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (i) Fuji, K.; Kinoshita, N.; Tanaka K.; Kawabata, T. Chem. Commun. 1999, 2289. (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
28. For some related examples, see: (a) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426. (b) Alexakis, A.: Polet, D. Org. Lett. 2004, 6, 3529. (c) Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794. (d) Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797. (e) Lipowsky, G.; Helmchen G. Chem. Commun. 2004, 116. (f) Fisher, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1629. (g) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426. (h) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (i) Fuji, K.; Kinoshita, N.; Tanaka K.; Kawabata, T. Chem. Commun. 1999, 2289. (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
29. For some related examples, see: (a) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426. (b) Alexakis, A.: Polet, D. Org. Lett. 2004, 6, 3529. (c) Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794. (d) Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797. (e) Lipowsky, G.; Helmchen G. Chem. Commun. 2004, 116. (f) Fisher, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1629. (g) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426. (h) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (i) Fuji, K.; Kinoshita, N.; Tanaka K.; Kawabata, T. Chem. Commun. 1999, 2289. (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
30. For some related examples, see: (a) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426. (b) Alexakis, A.: Polet, D. Org. Lett. 2004, 6, 3529. (c) Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794. (d) Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797. (e) Lipowsky, G.; Helmchen G. Chem. Commun. 2004, 116. (f) Fisher, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1629. (g) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426. (h) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (i) Fuji, K.; Kinoshita, N.; Tanaka K.; Kawabata, T. Chem. Commun. 1999, 2289. (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
31. For some related examples, see: (a) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426. (b) Alexakis, A.: Polet, D. Org. Lett. 2004, 6, 3529. (c) Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794. (d) Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797. (e) Lipowsky, G.; Helmchen G. Chem. Commun. 2004, 116. (f) Fisher, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1629. (g) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426. (h) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (i) Fuji, K.; Kinoshita, N.; Tanaka K.; Kawabata, T. Chem. Commun. 1999, 2289. (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
32. For some related examples, see: (a) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426. (b) Alexakis, A.: Polet, D. Org. Lett. 2004, 6, 3529. (c) Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794. (d) Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797. (e) Lipowsky, G.; Helmchen G. Chem. Commun. 2004, 116. (f) Fisher, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1629. (g) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426. (h) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164. (i) Fuji, K.; Kinoshita, N.; Tanaka K.; Kawabata, T. Chem. Commun. 1999, 2289. (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
33. For our studies on the iridium-catalyzed reaction, see: (a) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054. (b) Kanayama, T.; Yoshida, K.; Miyabe, H.; Kimachi, T.; Takemoto, Y. J. Org. Chem. 2003, 68, 6197.
34. For our studies on the iridium-catalyzed reaction, see: (a) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054. (b) Kanayama, T.; Yoshida, K.; Miyabe, H.; Kimachi, T.; Takemoto, Y. J. Org. Chem. 2003, 68, 6197.
35. Miyabe, H.; Yoshida, K. Matsumura, A.; Yamauchi, M.; Takemoto, Y. Synlett 2003, 567.
36. Castagnolo, D.; Armaroli, S.; Corelli, F.; Botta, M. Tetrahedron: Asymmetry 2004, 15, 941.
37. Miyabe, H.; Matsumura, A.; Yoshida, K.; Yamauchi, M.; Takemoto, Y. Synlett 2004, 2123.
38. Yoshioka, M.; Kawakita, T.; Ohno, M. Tetrahedron Lett. 1989, 30, 1657.
39. Oxime ethers have emerged as excellent radical acceptors. See: (a) McNabb, S. B.; Ueda, M.; Naito, T. Org. Lett. 2004, 6, 1911.
40. Diastereoseclective addition of organometallic reagents to oxime ethers: (b) Cooper, T. S.; Laurent, P.; Moody, C. J.; Takle, A. K. Org. Biomol. Chem. 2004, 2, 265. (c) Gallagher, P. T.; Hunt, J. C. A.; Lightfoot, A. P.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1997, 2633.
41. Diastereoseclective addition of organometallic reagents to oxime ethers: (b) Cooper, T. S.; Laurent, P.; Moody, C. J.; Takle, A. K. Org. Biomol. Chem. 2004, 2, 265. (c) Gallagher, P. T.; Hunt, J. C. A.; Lightfoot, A. P.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1997, 2633.