Ir-catalyzed asymmetric allylic amination using chiral diaminophosphine oxides

Tetrahedron Letters

Volumn 47, Issue 49, 2006, Pages 8737-8740

  Nemoto, Tetsuhiro ^a   Sakamoto, Tatsurou ^a   Matsumoto, Takayoshi ^a   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Asymmetric allylic amination; Asymmetric catalysis; Diaminophosphine oxide; Iridium

Indexed keywords

AMINE; CARBONIC ACID; FLUOROPHOSPHATE; IRIDIUM; PHOSPHINE OXIDE DERIVATIVE;

AMINATION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHIRALITY; REACTION ANALYSIS;

EID: 33750471192     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.003     Document Type: Article

References (49)

1. For a general review, see:. Ojima I. Catalytic Asymmetric Synthesis II (2000), Wiley-VCH, New York
2. For reviews, see:. Trost B.M. Chem. Pharm. Bull. 50 (2002) 1-14
3. Trost B.M., and Crawley M.L. Chem. Rev. 103 (2003) 2921-2943
4. Hayashi T., Yamamoto A., Ito Y., Nishioka E., Miura H., and Yanagi K. J. Am. Chem. Soc. 111 (1989) 6301-6311
5. Trost B.M., and Bunt R.C. J. Am. Chem. Soc. 116 (1994) 4089-4090
6. Evans D.A., Campos K.R., Tedrow J.S., Michael F.E., and Gagné M.R. J. Org. Chem. 64 (1999) 2994-2995
7. You S.-L., Zhu X.-Z., Lou Y.-M., Hou X.-L., and Dai L.-X. J. Am. Chem. Soc. 123 (2001) 7471-7472
8. Mori M., Nakanishi M., Kajishima D., and Sato Y. J. Am. Chem. Soc. 125 (2003) 9801-9807
9. Uozumi Y., Tanaka H., and Shibatomi K. Org. Lett. 6 (2004) 281-283
10. Takahashi K., Nakano H., and Fujita R. Tetrahedron Lett. 46 (2005) 8927-8930
11. Ohmura T., and Hartwig J.F. J. Am. Chem. Soc. 124 (2002) 15164-15165
12. Kiener C.A., Shu C., Incarvito C., and Hartwig J.F. J. Am. Chem. Soc. 125 (2003) 14272-14273
13. Shu C., Leiner A., and Hartwig J.F. Angew. Chem., Int. Ed. 43 (2004) 4797-4800
14. Tissot-Croset K., Polet D., and Alexakis A. Angew. Chem., Int. Ed. 43 (2004) 2426-2428
15. Lipowsky G., and Helmchen G. Chem. Commun. (2004) 896-897
16. Miyabe H., Matsumura A., Moriyama K., and Takemoto Y. Org. Lett. 6 (2004) 4631-4634
17. Weihohen R., Dahnz A., Tverskoy O., and Helmchen G. Chem. Commun. (2005) 3541-3543
18. Polet D., and Alexakis A. Org. Lett. 7 (2005) 1621-1624
19. Leitner A., Shekhar S., Pouy M.J., and Hartwig J.F. J. Am. Chem. Soc. 127 (2005) 15506-15514
20. Weihohen R., Tverskoy O., and Helmchen G. Angew. Chem., Int. Ed. 45 (2006) 5546-5549
21. Ru catalyst:. Matsushima Y., Onitsuka K., Kondo T., Mitsudo T., and Takahashi S. J. Am. Chem. Soc. 123 (2001) 10405-10406
22. Ni catalyst:. Bekowitz D.B., and Maiti G. Org. Lett. 6 (2004) 2661-2664
23. Enantiospecific allylic amination using Rh catalyst:. Evans P.A., Robinson J.E., and Nelson J.D. J. Am. Chem. Soc. 121 (1999) 6761-6762
24. Nemoto T., Matsumoto T., Masuda T., Hitomi T., Hatano K., and Hamada Y. J. Am. Chem. Soc. 126 (2004) 3690-3691
25. Nemoto T., Masuda T., Matsumoto T., and Hamada Y. J. Org. Chem. 70 (2005) 7172-7178
26. Nemoto T., Fukuda T., Matsumoto T., Hitomi T., and Hamada Y. Adv. Synth. Catal. 347 (2005) 1504-1506
27. Nemoto T., Jin L., Nakamura H., and Hamada Y. Tetrahedron Lett. 47 (2006) 6577-6581
28. Nemoto T., Masuda T., Akimoto Y., Fukuyama T., and Hamada Y. Org. Lett. 7 (2005) 4447-4450
29. For other examples of transition-metal catalysis using diaminophosphine oxides, see:. Ackermann L., and Born R. Angew. Chem., Int. Ed. 44 (2005) 2444-2447
30. Ackermann L., Born R., Spatz J.H., and Meyer D. Angew. Chem., Int. Ed. 44 (2005) 7216-7219
31. Ackermann L., Althammer A., and Born R. Angew. Chem., Int. Ed. 45 (2006) 2619-2622
32. For other examples of transition metal-catalyzed asymmetric reactions using chiral phosphine oxides, see:. Jiang X.-B., Minnaard A.J., Hessen B., Feringa B.L., Duchateau A.L.L., Andrien J.G.O., Boogers J.A.F., and de Vries J.G. Org. Lett. 5 (2003) 1503-1506
33. Dai W.-M., Yeung K.K.Y., Leung W.H., and Haynes R.K. Tetrahedron: Asymmetry 14 (2003) 2821-2826
34. Bigeault J., Giordano L., and Buono G. Angew. Chem., Int. Ed. 44 (2005) 4753-4757
35. For a review on chiral phosphine oxide ligands, see:. Dubrovina N.V., and Börner A. Angew. Chem., Int. Ed. 43 (2004) 5883-5886
36. For the pioneering work on Ir-catalyzed allylic substitutions, see:. Takeuchi R., and Kashio M. Angew. Chem., Int. Ed. 36 (1997) 263-265
37. Takeuchi R., and Kashio M. J. Am. Chem. Soc. 120 (1998) 8647-8655
38. Takeuchi R., Ue N., Tanabe K., Yamashita K., and Shiga N. J. Am. Chem. Soc. 123 (2001) 9525-9534
39. Takeuchi R. Synlett 12 (2002) 1954-1965
40. For other recent representative examples of Ir-catalyzed asymmetric allylic substitution reactions:. Lopez F., Ohmura T., and Hartwig J.F. J. Am. Chem. Soc. 125 (2003) 3426-3427
41. Kanayama T., Yoshida K., Miyabe H., and Takemoto Y. Angew. Chem., Int. Ed. 42 (2003) 2054-2056
42. Lipowsky G., Miller N., and Helmchen G. Angew. Chem., Int. Ed. 43 (2004) 4595-4597
43. Kinoshita N., Marx K.H., Tanaka K., Tsubaki K., Kawabata T., Yoshikai N., Nakamura E., and Fuji K. J. Org. Chem. 69 (2004) 7960-7964
44. Graening T., and Hartwig J.F. J. Am. Chem. Soc. 127 (2005) 17192-17193
45. Polet D., Alexakis A., Tissot-Croset K., Corminboeuf C., and Ditrich K. Chem. Eur. J. 12 (2006) 3596-3609
46. Lyothier I., Defieber C., and Carreira E.M. Angew. Chem., Int. Ed. 45 (2006) 6204-6207
47. Although the role of hexafluorophosphate anion is unknown, we speculate that, at the present stage, a cationic iridium complex might be formed by the anion exchange between hexafluorophosphate ion and a coordinated species around the Ir metal, resulting in the increased reactivity. Investigation of the mechanism is ongoing.
48. R 15.1 min [(R)-isomer] and 17.4 min [(S)-isomer], detection at 254 nm).
49. There was no improvement in the enantioselectivity when the reaction was performed at a lower temperature.