Stereoselective synthesis of axially chiral N-C bonds in N-aryl indoles

Organic Letters

Volumn 8, Issue 6, 2006, Pages 1097-1100

  Kamikawa, Ken ^a   Kinoshita, Shunsuke ^a   Matsuzaka, Hiroyuki ^a   Uemura, Motokazu ^b  

^a Osaka Prefecture University   (Japan)

^b KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646462590     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0529997     Document Type: Article

References (30)

1. (a) Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131.
2. (b) Tetrahedron Symposium in-print on Axially Chiral Amide; Clayden, J. Ed.; Tetrahedron 2004, 60, 4325.
3. Bennett, D. J.; Pickering, P. L.; Simpkins, N. S. Chem. Commun. 2004, 1392.
4. (a) Harta, T.; Koide, H.; Taniguchi, N.; Uemura, M. Org. Lett. 2000, 2, 1907.
5. (b) Koide, H.; Hata, T.; Uemura, M. J. Org. Chem. 2002, 67, 1929.
6. (a) Kitagawa, O.; Takashi, M.; Yoshikawa, M.; Taguchi, T. J. Am. Chem. Soc. 2005, 127, 3676.
7. (b) Kitagawa, O.; Kohriyama, M.; Taguchi, T. J. Org. Chem. 2002, 67, 8682.
8. Terauchi, J.; Curran, D. P. Tetrahedron: Asymmetry 2003, 14, 587.
9. Mino, T.; Tanaka, Y.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2001, 12, 2435.
10. Bringmann, G.; Tasler, S.; Endress, H.; Kraus, J.; Messer, K.; Wohlfarth, M.; Lobin, W. J. Am. Chem. Soc. 2001, 123, 2703.
11. (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 852.
12. (b) Hartwig, J. F. Acc. Chem. Res. 1998, 31. 805.
13. (a) Seki, K.; Ohkura, K.; Terashima, M.; Kanaoka, Y. Heterocycles 1994, 37, 993.
14. (b) Smith, W. J., III; Sawyer, S. Tetrahedron Lett. 1996, 37, 299.
15. (c) Astruc, D.; Balas, L.; Jhurry, D.; Latxague, L.; Grelier, S.; Morel, Y.; Hamdai, M.; Ardolin, N. Bull. Soc. Chim. Fr. 1990, 401.
16. (d) Semmelhack, M. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkenson, G., Eds.; Pergamon: New York, 1995; Vol. 12, p 979.
17. (e) Semmelhack, M. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; p 517.
18. Maiorana, S.; Baldoli, C.; Del Buttero, P.; Di Ciolo, M.; Papagni, A. Synthesis 1998, 735.
19. Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1996, 37, 6359.
20. 20% of the starting material was recovered, and 25% of decomplexed product was obtained.
21. Uemura, M.; Nishimura, H.; Kamikawa, K.; Shiro, M. Inorg. Chim. Acta 1994, 222, 63.
22. HPLC conditions: chiralcel OD; hexane/2-propanol = 9:1; flow rate of 1.0 mL/min; column temperature = 40 °C; UV detector = 254 nm, retention time, racemate, 5.96 min for (+)-isomer and 6.74 min for (-)-isomer.
23. (a) Kamikawa, K.; Sakamoto, T.; Tanaka, Y.; Uemura, M. J. Org. Chem. 2003, 68, 9356.
24. (b) Kamikawa, K.; Sakamoto, T.; Uemura, M. Synlett 2003, 516.
25. (a) Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1989; Vol. 1, p 99.
26. (b) Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1991; Vol. 2, p 1.
27. (c) Uemura, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1991; Vol. 2, p 195.
28. (d)Semmelhack, M. F. In Comprehensive Organometallic Chemistry II; Abel, E. D., Stone, F. G. A., Wilkinson, Eds.; Pergamon Press: Oxford, 1995; Vol. 12, p 979.
29. (e) Davies, S. G.; McCarthy, T. D. In Comprehensive Organometallic Chemistry II; Abel, E. D.; Stone, F. G. A., Wilkinson, Eds.; Pergamon Press: Oxford, 1995; Vol. 12, p 1039.
30. Nechvatal, G.; Widdowson, D. A. J. Chem. Soc., Chem. Commun. 1982, 467.