Enantioselective Friedel-Crafts type addition of indoles to nitro-olefins using a chiral hydrogen-bonding catalyst - Synthesis of optically active tetrahydro-β-carbolines

Organic and Biomolecular Chemistry

Volumn 3, Issue 14, 2005, Pages 2566-2571

  Zhuang, Wei ^a   Hazell, Rita G ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CRYSTALLIZATION; HYDROGEN BONDS; MOLECULAR STRUCTURE; OLEFINS; OPTICAL PROPERTIES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

INDOLES; NITRO-OLEFINS; RECRYSTALLIZATIONS; X-RAY STRUCTURE;

NITROGEN COMPOUNDS;

EID: 23044472914     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b505220c     Document Type: Article

References (46)

1. For a review of asymmetric Michael addition to nitroalkenes, see: O. M. Berner, L. Tedeschi and D. Enders, Eur. J. Org. Chem., 2002, 1877.
2. For a review of asymmetric Friedel-Crafts alkylation, see: M. Bandini, M. Melloni and A. Umani-Ronchi, Angew. Chem., Int. Ed., 2004, 43, 550.
3. See, for example: K. Lee and D. Y. Oh, Tetrahedron Lett., 1988, 29, 2977;
4. T. Ohe and S. Uemura, Tetrahedron Lett., 2002, 43, 1269;
5. K. Manabe, N. Naoyama and S. Kobayashi, Adv. Synth. Catal., 2001, 343, 174;
6. J. S. Yadav, S. Abraham, B. V. S. Reddy and G. Sabitha, Synthesis, 2001, 2165;
7. M. Bandini, P. Melchiorre, A. Melloni and A. Umani-Ronchi, Synthesis, 2002, 1110;
8. H. Firouzabadi, N. Iranpour and N. Nowrouzi, Chem. Commun., 2005, 789.
9. See, for example: M. Bandini, M. Fagioli and A. Umani-Ronchi, Adv. Synth. Catal., 2004, 346, 545;
10. G. Dessole, R. P. Herrera and A. Ricci, Synlett, 2004, 2374.
11. For reviews, see, for example: P. M. Pihko, Angew. Chem., Int. Ed., 2004, 43, 2062;
12. P. R. Schreiner, Chem. Soc. Rev., 2003, 32, 289;
13. P. I. Dalko and L. Moisan, Angew. Chem., Int. Ed., 2004, 43, 5138.
14. J. M. Betancort and C. F. Barbas, III, Org. Lett., 2001, 3, 3737;
15. A. Alexakis and O. Andrey, Org. Lett., 2002, 4, 3611;
16. J. M. Betancort, K. Sakthivel, R. Thayumanavan and C. F. Barbas, III, Tetrahedron Lett., 2001, 42, 4441;
17. A. J. A. Cobb, D. A. Longbottom, D. M. Shaw and S. V. Ley, Chem. Commun., 2004, 1808;
18. B. List, P. Pojarliev and H. Martin, Org. Lett., 2001, 3, 2423;
19. D. Enders and A. Seki, Synlett, 2002, 26;
20. W. Wang, J. Wang and H. Li, Angew. Chem., Int. Ed., 2005, 44, 1369.
21. T. Okino, Y. Hoashi and Y. Takemoto, J. Am. Chem. Soc., 2003, 125, 12672;
22. Y. Hoashi, T. Yabuta and Y. Takemoto, Tetrahedron Lett., 2004, 45, 9185.
23. H. Li, Y. Wang, L. Tang and L. Deng, J. Am. Chem. Soc., 2004, 126, 9906;
24. H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman and L. Deng, Angew. Chem., Int. Ed., 2005, 44, 105.
25. For a review, see, for example: D. Lucet, T. L. Gall and C. Mioskowski, Angew. Chem., Int. Ed., 1998, 37, 2581.
26. Synthesis of chiral diamines, see, for example: E. J. Corey, R. Imwinkelried, S. Pikul and Y. B. Xiang, J. Am. Chem. Soc., 1989, 111, 5493;
27. E. J. Corey, D.-H. Lee and S. Sarshar, Tetrahedron: Asymmetry, 1995, 6, 3;
28. S. Roland and P. Mangeney, Eur. J. Org. Chem, 2000, 611;
29. S. Rolan and P. Mangeney, Synthesis, 1999, 228.
30. For review of Calabar alkaloids, see, for example: S. Takano and K. Ogasawara, Alkaloids, 1989, 36, 225;
31. B. Robinson, Alkaloids, 1971, 13, 213.
32. For reviews of pharmacology, see: N. H. Greig, X. F. Pei, T. T. Soncrant, D. K. Ingram and A. Brossi, Med. Res. Rev., 1995, 15, 3.
33. 2 gave no conversion.
34. The slightly lower enantiomeric excess after column chromatography is due to fact that some of the Friedel-Crafts reactions never proceed to completion and the remaining starting materials react during the chromatography procedure catalyzed by silica gel to give a racemic product, thereby lowering the enantiomeric excess.
35. Silica gel-catalyzed reaction, see, for example: H. Kotsuki, K. Hayashida, T. Shimanouchi and H. Nishizawa, J. Org. Chem., 1996, 61, 984.
36. E. D. Cox and J. M. Cook, Chem. Rev., 1995, 95, 1797;
37. M. S. Taylor and E. N. Jacobsen, J. Am. Chem. Soc., 2004, 126, 10588 and refs. cited therein.
38. K. W. Bentley, Nat. Prod. Rep., 2004, 21, 395 and refs. cited therein.
39. For a recent structure of a benzaldehyde-chiral biaryl diol complex, see: A. K. Unni, N. Takenaka, H. Yamamoto and V. H. Rawal, J. Am. Chem. Soc., 2005, 127, 1336.
40. C. A. Merlic, Y. You, D. M. McInnes, A. L. Zechman, M. M. Miller and Q. Deng, Terahedron, 2001, 57, 5199;
41. P. J. Beswick, C. S. Greenwood, T. J. Mowlem, G. Nechvatal and D. A. Widdowson, Terahedron, 1988, 44, 7235.
42. S. E. Denmark and L. Marcin, J. Org. Chem., 1995, 60, 3221;
43. S. E. Denmark and L. Marcin, J. Org. Chem., 1993, 58, 3580.
44. D. Rogers, Acta Crystallogr., Sect. A, 1981, 37, 734.
45. (a) R. H. Blessing, J. Appl. Crystallogr., 1989, 22, 396;
46. (b) H. D. Flack, Acta Crystallogr., Sect. A, 1983, 39, 876.