Practical highly enantioselective synthesis of propargylamines through a copper-catalyzed one-pot three-component condensation reaction

Chemistry - A European Journal

Volumn 12, Issue 16, 2006, Pages 4380-4392

  Gommermann, Nina ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Alkynes; Asymmetric catalysis; C H activation; Multicomponent reactions; Organocatalysis; Propargylamine

Indexed keywords

BROMINE COMPOUNDS; COPPER COMPOUNDS; PHASE TRANSITIONS; REACTION KINETICS; STEREOCHEMISTRY;

ASYMMETRIC CATALYSIS; C-H ACTIVATION; MULTICOMPONENT REACTIONS; ORGANOCATALYSIS; PROPARGYLAMINE;

AMINES;

ALDEHYDE; ALKYNE; AMINE; BROMIDE; COPPER; CUPRIC BROMIDE; DRUG DERIVATIVE; PARGYLINE; PROPARGYLAMINE; PROPYLAMINE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ALKYNES; AMINES; BROMIDES; CATALYSIS; COPPER; PARGYLINE; PROPYLAMINES; STEREOISOMERISM;

EID: 33744823250     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501233     Document Type: Article

References (72)

1. For recent three-component reactions: a) S. Kamijo, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124.11940;
2. S. Kamijo, T. Jin, Y. Yamamoto, J. Am. Chem. Soc. 2001, 123, 9453;
3. b) F. Bertozzi, M. Gustafsson, R. Olsson, Org. Lett. 2002, 4, 4333;
4. c) G. W. Kabalka, Z. Wu, Y. Ju, Org. Lett. 2002, 4, 3415;
5. d) T.-P. Loh, S.-L. Chen, Org. Lett. 2002, 4, 3647;
6. e) A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300;
7. Angew. Chem. Int. Ed. 2000, 39, 3168;
8. f) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827;
9. g) U. Bora, A. Saikia, R. C. Boruah, Org. Lett. 2003, 5, 435;
10. h) R. Dhawan, R. D. Dghaym, B. A. Arndtsen, J. Am. Chem. Soc. 2003, 125, 1474;
11. i) C. Cao, Y. Shi, A. L. Odom, J. Am. Chem. Soc. 2003, 125, 2880;
12. j) S. J. Patel, T. F. Jamison, Angew. Chem. 2003, 115, 1402;
13. Angew. Chem. Int. Ed. 2003, 42, 1364;
14. k) J. R. Porter, J. F. Traverse, A. H. Hoveyda, M. L. Snapper, J. Am. Chem. Soc. 2001, 123, 10409;
15. for an excellent review on multicomponent reactions, see: D. J. Ramón, M. Yus, Angew. Chem. 2005, 117, 1628;
16. Angew. Chem. Int. Ed. 2005, 44, 1602.
17. a) B. M. Trost, Angew. Chem. 1995, 107, 285;
18. Angew. Chem. Int. Ed. Engl. 1995, 34, 259;
19. b) B. M. Trost, Science 1991, 254, 1471.
20. a) A. Strecker, Justus Liebigs Ann. Chem. 1850, 75, 27;
21. b) H. Kunz, Stereoselective Synthesis (Houben-Weyl), Vol. 3 (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer), Thieme, Stuttgart, 1996, p. 1931.
22. G. Habermehl, P. E. Hammann, Naturstoffchemie, Springer, Heidelberg, 1992.
23. a) M. A. Huffman, N. Yasuda, A. E. DeCamp, E. J. J. Grabowski, J. Org. Chem. 1995, 60, 1590;
24. b) M. Konishi, H. Ohkuma, T. Tsuno, T. Oki, G. D. VanDuyne, J. Clardy, J. Am. Chem. Soc. 1990, 112, 3715.
25. a) N. Gommermann, C. Koradin, K. Polborn, P. Knochel, Angew. Chem. 2003, 115, 5941;
26. Angew. Chem. Int. Ed. 2003, 42, 5763;
27. b) N. Gommermann, P. Knochel, Chem. Commun. 2004, 2324;
28. c) H. Dube, N. Gommermann, P. Knochel, Synthesis 2004, 12, 2015.
29. a) for an excellent review, see: C. Wei, Z. Li, C.-J. Li, Synlett 2004, 1472;
30. b) C M. Wei, C.-J. Li, J. Am. Chem. Soc. 2003, 125, 9584;
31. c) L. C. Akullian, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2003, 115, 4376;
32. Angew. Chem. Int. Ed. 2003, 42, 4244;
33. d) S. Sakaguchi, T. Kubo, Y. Ishii, Angew. Chem. 2001, 113, 2602:
34. Angew. Chem. Int. Ed. 2001, 40, 2534;
35. e) L. Shi, Y.-Q. Tu, M. Wang, F.-M. Zhang, C.-A. Fan, Org. Lett. 2004, 6, 1001;
36. f) C. M. Wei, C.-J. Li, J. Am. Chem. Soc. 2002, 124, 5638;
37. g) C. M. Wei, Z. G. Li, C.-J. Li, Org. Lett. 2003, 5, 4473;
38. h) Z. Li, C.-J. Li, Org. Lett. 2004, 6, 4997;
39. i) J. F. Traverse, A. H. Hoveyda, M. L. Snapper, Org. Lett. 2003, 5, 3273;
40. j) for the preparation of chiral propargylic alcohols see: D. E. Frantz, R. Faessler, E. M. Carreira, J. Am. Chem. Soc. 2000, 122, 1806.
41. a) J. M. Valk, G. A. Whitlock, T. P. Layzell, J. M. Brown, Tetrahedron: Asymmetry 1995, 6, 2593;
42. b) E. Fernandez, K. Maeda, M. W. Hooper, J. M. Brown, Chem. Eur. J. 2000, 6, 1840.
43. P. J. Kocienski, Protective Groups, Thieme, Stuttgart, 3rd ed., 2003.
44. a) C. Koradin, K. Polborn, P. Knochel, Angew. Chem. 2002, 114, 2651;
45. Angew. Chem. Int. Ed. 2002, 41, 2535;
46. b) C. Koradin, N. Gommermann, P. Knochel, Chem. Eur. J. 2003, 9, 2797.
47. a) K. Sonogashira in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming, G. Pattenden), Pergamon Press, New York, 1991;
48. b) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 4467;
49. c) for an excellent review, see: R. R. Tykwinski, Angew. Chem. 2003, 115, 1604;
50. Angew. Chem. Int. Ed. 2003, 42, 1566.
51. a) F. Bois, D. Gardette, J.-C. Gramain, Tetrahedron Lett. 2000, 41, 8769;
52. b) A. M. Chippindale, S. G. Davies, K. Iwamoto, R. M. Parkin, C. A. P. Smethurst, A. D. Smith, H. Rodriguez-Solla, Tetrahedron 2003, 59, 3253;
53. c) J. F Hayes, M. Shipman, H. Twin, Chem. Commun. 2001, 1784;
54. d) B. Guilloteau-Bertin, D. Compère, L. Gil, C. Marazano, B. C. Dao, Eur. J. Org. Chem. 2000, 1391;
55. e) M. Shimizu, A. Arai, T. Fujisawa, Heterocycles, 2000, 52, 137;
56. f) M. T. Reding, S. L. Buchwald, J. Org. Chem. 1998, 63, 6344;
57. g) G. Paudey, P. Das, Tetrahedron Lett. 1997, 38, 9073;
58. h) N. Yamazaki, C. Kibayashi, Tetrahedron Lett. 1997, 38, 4623;
59. i) S. Fréville, J. P. Célérier, V.M. Thuy, G. Lhommet, Tetrahedron: Asymmetry 1995, 6, 2651;
60. j) H. Suzuki, S. Aoyagé, C. Kibayashi, Tetrahedron Lett. 1994, 35, 6119;
61. k) D. Enders, J. Tiebes, Liebigs Ann. Chem. 1993, 173; 1)
62. H. Waldmann, M. Braun, M. Dräger, Angew. Chem. 1990, 102; 1445;
63. Angew. Chem. Int. Ed. Engl. 1990, 29, 1468.
64. M. Yamaguchi, I. Hirao, Tetrahedron Lett. 1983, 24, 391.
65. D. L. Hughes, Org. React. 1992, 42, 335.
66. CCDC-216200 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
67. a) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088;
68. Angew. Chem. Int. Ed. 1998, 37, 2922;
69. b) D. Guillaneux, S.-H. Zhao, O. Samuel, D. Rainford, H. B. Kagan, J. Am. Chem. Soc. 1994, 116, 9430.
70. A. Padwa, A. Zanka, M. P. Cassidy, J. M. Harris, Tetrahedron 2003, 59, 4939.
71. J. M. Salvino, M. Mervic, H. J. Mason, T. Kiesow, D. Teager, J. Airey, R. Labaudiniere, J. Org. Chem. 1999, 64, 1823.
72. T. Kamikawa, T. Hayashi, J. Org. Chem. 1998, 63, 8922.