Expanding the scope of cinchona alkaloid-catalyzed enantioselective α-aminations of oxindoles: A versatile approach to optically active 3-amino-2-oxindole derivatives

Journal of Organic Chemistry

Volumn 74, Issue 23, 2009, Pages 8935-8938

  Bui, Tommy ^a   Borregan, Mar ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CHIRAL CENTERS; CINCHONA ALKALOID; ENANTIOSELECTIVE; HIGH YIELD; OPTICALLY ACTIVE; OXINDOLES;

AMINES; ENANTIOSELECTIVITY;

AMINATION;

CARBON; CINCHONA ALKALOID; NITROGEN; OXINDOLE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY;

AMINATION; CATALYSIS; CINCHONA ALKALOIDS; INDOLES; STEREOISOMERISM;

EID: 72249084937     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902039a     Document Type: Article

References (59)

1. (a) Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209.
2. (b) Rahman, A. U.; Basha, A. Indole Alkaloid; Harwood Academic Publishers: Amsterdam, 1997.
3. (a) Hewawasam, P.; Erway, M.; Moon, S. L.; Knipe, J.; Weiner, H.; Boissard, C. G.; Post-Munson, D. J.; Gao, Q.; Huang, S.; Gribkoff, V. K.; Meanwell, N. A. J. Med. Chem. 2002, 45, 1487.
4. (b) Suzuki, H.; Morita, H.; Shiro, M.; Kobayashi, J. I. Tetrahedron 2004, 60, 2489.
5. (c) Leugn, C.; Tomaszewski, M.; Woo, S. (Astrazeneca AB, Sweden); U.S. Patent Appl. Publ. (2007), CODEN: USXXCO US 2007185179 A1 20070809; patent written in English, application US 2007-671153 20070205. Priority: US 2006-771119 20060207.
6. Synthesis of 3-hydroxy-2-oxindoles using transition metal asymmetric catalysis: (a) Toullec, P. Y.; Jagt, R. B. C.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. L. Org. Lett. 2006, 8, 2715.
7. (b) Shintani, R.; Inoue, M.; Hayashi, T. Angew. Chem., Int. Ed. 2006, 45, 3353.
8. (c) Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanesmasa, S. J. Am. Chem. Soc. 2006, 128, 16488.
9. (d) Tomita, D.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 6946.
10. (e) Grant, C. D.; Krische, M. J. Org. Lett. 2009, 7, 867.
11. (f) Itoh, J.; Han, S. B.; Krische, M. J. Angew. Chem., Int. Ed. 2009, 48, 6313.
12. (g) Lai, H.; Huang, Z.; Wu, Q.; Qin, Y. J. Org. Chem. 2009, 74, 283.
13. Preparation of 3-hydroxy or 3-amino-2-oxindoles by preparative HPLC separation of enantiomers: (a) Labroo, R. B.; Cohen, L. A. J. Org. Chem. 1990, 55, 4901.
14. (b) See ref 2c.
15. During the preparation of this paper, a related cinchona alkaloid-catalyzed α-amination of oxidoles was published online: Cheng, L.; Liu, Li.; Wang, D.; Chen, Y.-J. Org. Lett. 2009, 11, 3874.
16. Reviews on α-amination of carbonyl compounds: (a) Guillena, G.; Ramon, D. J. Tetrahedron: Asymmetry 2006, 17, 1465.
17. (b) Janey, J. M. Angew. Chem., Int. Ed. 2005, 44, 4292.
18. (c) Erdick, E. Tetrahedron 2004, 60, 8747.
19. Amine-catalyzed α-amination of aldehydes and ketones: (a) Kumaragurbaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254.
20. (b) Bogevig, A.; Juhl, K.; Kumaragurbaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
21. (c) List, B. J. Am. Chem. Soc. 2002, 124, 5656.
22. (d) Chowdari, N. S.; Barbas, C. F. III. Org. Lett. 2005, 7, 867.
23. (e) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448.
24. (f) Dahlin, N.; Bogevig, A.; Adolfson, H. Adv. Synth. Catal. 2004, 346, 1101.
25. Organocatalytic enantioselective α-amination of β-ketoesters and derivatives thereof: (a) Pihko, P. M.; Pohjakallio, A. Synlett 2004, 12, 2115.
26. (b) Saaby, S.; Bella, M.; Jorgensen, K. A. J. Am. Chem. Soc. 2004, 126, 8120.
27. (c) Liu, X.; Li, H.; Deng, L. Org. Lett. 2005, 7, 167.
28. (d) Terada, M.; Nakano, M.; Ube, H. J. Am. Chem. Soc. 2006, 128, 16044.
29. (d) Liu, Y; Melgar-Fernandez, R.; Juaristi, E. J. Org. Chem. 2007, 72, 1522.
30. For related C-C bond-forming reactions involving oxindoles as nucleophiles in organocatalysis, see: (a) Bui, T.; Syed, S.; Barbas, C. F. III. J. Am. Chem. Soc. 2009, 131, 8756.
31. (b) He, R.; Ding, C.; Maruoka, K. Angew. Chem., Int. Ed. 2009, 48, 4559.
32. (c) Chen, X.-H.; Wei, Q.; Luo, S.-W.; Xiao, H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 13819-13825.
33. (d) Galzerano, P.; Bencivenni, G.; Pesciaioli, F.; Mazzanti, A.; Giannichi, B.; Sambri, L.; Bartoli, G.; Melchiorre, P. Chem.; - Eur. J. 2009, 15, 7846.
34. (e) Duffey, T. A.; Shaw, S. A.; Vedejs, E. J. Am. Chem. Soc. 2009, 131, 14.
35. (f) Shaw, S. A.; Aleman, P.; Christy, J.; Kampf, J. W.; Va, P.; Vedejs, E. J. Am. Chem. Soc. 2006, 128, 925.
36. Leading references for C-C bond-forming reactions of oxindoles involving transition metal catalysis: (g) Kato, Y.; Furutachi, M.; Chen, Z.; Mitsunuma, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 9168.
37. (h) Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477.
38. (i) Doumay, A. B.; Hatanaka, K.; Kodanko, J. J.; Oestreich, M.; Overman, L. E.; Pfeifer, L. A.; Weiss, M. M. J. Am. Chem. Soc. 2003, 125, 6261.
39. (j) Trost, B. M.; Frederiksen, M. U. Angew. Chem., Int. Ed. 2005, 44, 308.
40. (k) Trost, B. M.; Zhang, Y. J. Am. Chem. Soc. 2006, 126, 4590.
41. (l) Trost, B. M.; Zhang, Y. J. Am. Chem. Soc. 2007, 129, 14548.
42. (m) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402.
43. (n) Hills, I. D.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 3921.
44. (o) Kozlowski, M. C.; Linton, E. C. J. Am. Chem. Soc. 2008, 130, 16162.
45. Aldol and Mannich reactions involving oxindoles as nucleophiles: (a) Ogawa, S.; Shibata, N.; Inagaki, J.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2007, 46, 8666.
46. (b) Tian, X.; Jiang, K.; Peng, J.; Du, W.; Chen, Y.-C. Org. Lett. 2008, 10, 3583.
47. For related cinchona alkaloid-catalyzed α-fluorination of oxindoles: Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2008, 47, 4157.
48. These optically active oxindoles are usually obtained through resolution or preparative HPLC separation; see ref 4.
49. We previously observed that the acidity of the C3 methine proton could be affected greatly by changing the protecting group on the oxindole nitrogen atom; see ref 9a.
50. Without a protecting group on the nitrogen atom and under identical conditions, 3a was obtained in 78% yield with 11% ee.
51. At -38°C, with catalyst 2b, product 3a was obtained in 25% yield with 65% ee after 24 h reaction.
52. The background reaction was significantly less in toluene than in methylene chloride, and this might, in part, account for the better ee observed in this solvent.
53. Dielectric constants and solvent polarity: (a) Abboud, J-L. M.; Taft, R. W. J. Phys. Org. 1979, 83, 412.
54. (b) Katritzky, A. R.; Fara, D. C.; Yang, H.; Tamm, K. Chem. Rew. 2004, 104, 175.
55. Attempts to solve this selectivity problem by changing the diethyl azodicarboxylate reagent failed. Specifically, 39 and 63% ee were obtained when dibenzyl azodicarboxylate and diisopropyl azodicarboxylate were used, respectively.
56. Use of di-tert-butyl azocarboxylate in Lewis acid catalyzed asymmetric amination: (a) Mashiko, T.; Hara, K.; Tanaka, D.; Fujiwara, Y.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 11342.
57. (b) Mashiko, T.; Kumagai, N.; Shibasaki, M. Org. Lett. 2008, 10, 2725.
58. Occasionally, N-Boc-protected oxindoles gave products with high ee. However, they are not as general as N-benzyl-protected counterparts. Compounds 3m and 3d were made in an attempt to obtain crystals for X-ray analysis. Unfortunately, these compounds did not yield satisfactory crystals.
59. See Supporting Information.