Proline-Catalyzed Asymmetric Addition Reaction of 9-Tosyl-3,4-dihydro- β-carboline with Ketones

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4301-4304

  Itoh, Takashi ^a   Yokoya, Masashi ^a   Miyauchi, Keiko ^a   Nagata, Kazuhiro ^a   Ohsawa, Akio ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

9 TOSYL 3,4 DIHYDRO BETA CARBOLINE; CARBOLINE DERIVATIVE; KETONE DERIVATIVE; PROLINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 0344927944     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol030103x     Document Type: Article

References (47)

1. (a) Gröger, H.; Wilken, J. Angew. Chem., Int. Ed. 2001, 40, 529-532.
2. (b) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726-3748.
3. (c) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495, and references therein.
4. (a) List, B. Synlett 2001, 1675-1686.
5. (b) List, B. Tetrahedron 2002, 58, 5573-5590.
6. (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615-1621.
7. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. 1971, 10, 496-497.
8. (c) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396.
9. (d) Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386-7387.
10. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573-575.
11. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267.
12. (g) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799.
13. (h) Alcaide, B.; Almendros, P. Angew. Chem., Int. Ed. 2003, 42, 858-860.
14. (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336-9337.
15. (b) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199-201.
16. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827-833.
17. (a) Yamaguchi, M.; Yokota, N.; Minami, T. J. Chem. Soc., Chem. Commun. 1991, 1088-1089.
18. (b) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423-2425.
19. (c) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975-2978.
20. (d) Enders, D.; Seki, A. Synlett 2002, 26-28.
21. (a) List, B. J. Am. Chem. Soc. 2002, 124, 5656-5657.
22. (b) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790-1793.
23. (c) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254-6255.
24. (c) Duthaler, R. O. Angew. Chem., Int. Ed. 2003, 42, 975-978.
25. Shi, M.; Jiang, J.-K.; Li, C.-Q. Tetrahedron Lett. 2001, 43, 127-130.
26. (a) Itoh, T.; Matsuya, Y.; Enomoto, Y.; Nagata, K.; Miyazaki, M.; Ohsawa, A. Tetrahedron 2001, 57, 7277-7289.
27. (b) Itoh, T.; Miyazaki, M.; Ikeda, S.; Nagata, K.; Yokoya, M.; Matsuya, Y.; Enomoto, Y.; Ohsawa, A. Tetrahedron 2003, 59, 3527-3536 and references therein.
28. The Chemistry of Heterocyclic Compounds; Saxton, J. E., Ed.; Wiley: Chichester, 1994; Part 4, supplement of Vol. 25.
29. (a) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797-1842 and references therein.
30. (b) Li, J.; Wang, T.; Yu, P.; Peterson, A.; Weber, R.; Soerens, D.; Grubisha, D.; Bennett, D.; Cook, J. M. J. Am. Chem. Soc. 1999, 121, 6998-7010.
31. (c) Yu, S.; Berner, O. M.; Cook, J. M. J. Am. Chem. Soc. 2000, 122, 7827-7828.
32. (a) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161-6171.
33. (b) Martin, S. F.; Clark, C. C.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236-3242.
34. (c) Martin, S. F.; Chen, K. X.; Eary, C. T. Org. Lett. 1999, 1, 79-81.
35. (d) Martin, S. F. Acc. Chem. Res. 2002, 35, 895-904.
36. (a) Meyers, A. I.; Sohda, T.; Loewe, M. F. J. Org. Chem. 1986, 51, 3108-3112.
37. (b) Meyers, A. I.; Miller, D. B.; White, F. H. J. Am. Chem. Soc. 1988, 110, 4778-4787.
38. (c) Beard, R. L.; Meyers, A. I. J. Org. Chem. 1991, 56, 2091-2096.
39. (d) Meyers, A. I.; Highsmith, T. K.; Buonora, P. T. J. Org. Chem. 1991, 56, 2960-2964.
40. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489-8490.
41. Rey, A. W.; Szarek, W. A. Can. J. Chem. 1992, 70, 2922-2928.
42. 2, but a small amount of water was detected by a coulometer in other solvents (0.70 equiv in acetone, 1.04 equiv in DMSO).
43. Reaction medium was cooled to -2°C because it was the lowest temperature at which the solvent remains liquid.
44. Waldmann, H.; Braun, M.; Weymann, M.; Gewehr, M. Tetrahedron 1993, 49, 397-416.
45. Kametani, T.; Hirai, Y.; Kajiwara, M.; Takahashi, T.; Fukumoto, K. Chem. Pharm. Bull. 1975, 23, 2634-2642.
46. Szántay, C.; Blaskó, G.; Honty, K.; Szabó, L.; Töke, L. Heterocycles 1977, 7, 155-160.
47. Substrate of the present reaction has the (Z)-imine structure; thus, the transition state was supposed to be similar to that of the aldol reaction (ref 3, Re face attack) rather than the one for the (E)-imine Mannich reaction (ref 4, Si face attack).