Formation of Quaternary Stereocenters by Copper-Catalyzed Michael Reactions with L-Valine Amides as Auxiliaries

Chemistry - A European Journal

Volumn 9, Issue 20, 2003, Pages 4862-4867

  Christoffers, Jens ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Amino acid derivative; Catalysis; Chirality; Michael addition; Stereoselectivity

Indexed keywords

CATALYSIS; COPPER; HYDROCARBONS; KETONES;

STEREOCENTERS;

STEREOCHEMISTRY;

1,3 DICARBONYL DERIVATIVE; ACETONE; AMIDE; CARBONYL DERIVATIVE; COPPER ACETATE; COPPER DERIVATIVE; KETONE; SOLVENT; UNCLASSIFIED DRUG; VALINE; VALINE DIETHYLAMIDE; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; ASYMMETRIC MICHAEL REACTION; CATALYSIS; CHIRALITY; ENVIRONMENTAL TEMPERATURE; LIGAND BINDING; METAL BINDING; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0142228974     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304937     Document Type: Article

References (57)

1. Reviews: a) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171-196;
2. b) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061;
3. c) J. Leonard, E. Díez-Barra, S. Merino, Eur. J. Org. Chem. 1998, 2051-2061;
4. d) Y. Yamamoto, S. G. Pyne, D. Schinzer, B. L. Feringa, J. F. G. A. Jansen, Methoden Org. Chem. (Houben-Weyl) 1995, E21b, 2011-2155;
5. e) B. E. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 771-806.
6. a) M. Sawamura, H. Hamashima, Y. Ito, Tetrahedron: Asymmetry 1991, 2, 593-596;
7. b) M. Sawamura, H. Hamashima, Y. Ito, J. Am. Chem. Soc. 1992, 114, 8295-8296;
8. c) M. Sawamura, H. Hamashima, Y. Ito, Tetrahedron 1994, 50, 4439-4454;
9. d) M. Sawamura, H. Hamashima, H. Shinoto, Y. Ito, Tetrahedron Lett. 1995, 36, 6479-6482;
10. e) M. Sawamura, H. Hamashima, Y. Ito, Bull. Chem. Soc. Jpn. 2000, 73, 2559-2562.
11. Reviews: a) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187-2209;
12. b) M. Kanai, M. Shibasaki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, Weinheim, 2000, pp. 569-592;
13. c) Y. Xu, K. Ohori, T. Ohshima, M. Shibasaki, Tetrahedron 2002, 58, 2585-2588;
14. d) H. Sasai, E. Emori, T. Arai, M. Shibasaki, Tetrahedron Lett. 1996, 37, 5561-5564.
15. Reviews: a) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597:
16. Reviews: a) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597:
17. b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401;
18. b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401;
19. c) K. Fuji, Chem. Rev. 1993, 93, 2037-2066;
20. d) S. F. Martin, Tetrahedron 1980, 36, 419-460.
21. a) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507;
22. b) S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473-8478;
23. c) N. Kumagai, S. Matsunaga, M. Shibasaki, Org. Lett. 2001, 3, 4251-4254;
24. d) R. Takita, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2002, 43, 4661-4665;
25. reviews: e) S. Matsunaga, T. Ohshima, M. Shibasaki, Adv. Synth. Catal. 2002, 344, 3-15;
26. f) M. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun. 2002, 1989-1999;
27. g) S. Harada, N. Kumagai, T. Kinoshita, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2582-2590.
28. a) Y. Hamashima, D. Hotta, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 11240-11241;
29. review: b) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726-1728; Angew. Chem. Int. Ed. 2003, 42, 1688-1690.
30. review: b) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726-1728; Angew. Chem. Int. Ed. 2003, 42, 1688-1690.
31. a) M. Pfau, G. Revial, A. Guingant, J. d'Angelo, J. Am. Chem. Soc. 1985, 107, 273-274;
32. b) C. Camara, D. Joseph, F. Dumas, J. d'Angelo, A. Chiaroni, Tetrahedron Lett. 2002, 43, 1445-1448;
33. reviews: c) J. d'Angelo, D. Desmaële, F. Dumas, A. Guingant, Tetrahedron: Asymmetry 1992, 3, 459-505;
34. d) L. Keller, C. Camara, A. Pinheiro, F. Dumas, J. d'Angelo, Tetrahedron Lett. 2001, 42, 381-383.
35. Reviews: a) J. Christoffers, Eur. J. Org. Chem. 1998, 1259-1266;
36. b) J. Christoffers, Synlett 2001, 723-732.
37. a) J. Christoffers, Liebigs Ann./Recl. 1997, 1353-1358;
38. b) J. Christoffers, A. Mann, Eur. J. Org. Chem. 1999, 1475-1479;
39. c) J. Christoffers, A. Mann, J. Pickardt, Tetrahedron 1999, 55, 5377-5388;
40. d) J. Christoffers, U. Rößler, Tetrahedron: Asymmetry 1998, 9, 2349-2357;
41. e) J. Christoffers, U. Rößler, Tetrahedron: Asymmetry 1999, 10, 1207-1215;
42. f) J. Christoffers, J. Prakt. Chem. 1999, 341, 495-498;
43. g) J. Christoffers, U. Rößler, J. Prakt. Chem. 2000, 342, 654-658;
44. h) J. Christoffers, U. Rößler, Tetrahedron 2001, 57, 1779-1783.
45. J. Christoffers, U. Rößler, T. Werner, Eur. J. Org. Chem. 2000, 701-705.
46. J. Christoffers, Y. Schulze, J. Pickardt, Tetrahedron 2001, 57, 1765-1769.
47. J. Christoffers, A. Mann, Chem. Eur. J. 2001, 7, 1014-1027.
48. J. Christoffers, A. Mann, Angew. Chem. 2000, 112, 2871-2874; Angew. Chem. Int. Ed. 2000, 39, 2752-2754.
49. J. Christoffers, A. Mann, Angew. Chem. 2000, 112, 2871-2874; Angew. Chem. Int. Ed. 2000, 39, 2752-2754.
50. J. Christoffers, H. Scharl, Eur. J. Org. Chem. 2002, 1505-1508.
51. a) K. Tomioka, W. Seo, K. Ando, K. Koga, Tetrahedron Lett. 1987, 28, 6637-6640;
52. b) K. Ando, W. Seo, K. Tomioka, K. Koga, Tetrahedron 1994, 50, 13081-13088.
53. a) J. Christoffers, H. Oertling, P. Fischer, W. Frey, Synlett 2002, 957-961;
54. b) J. Christoffers, H. Oertling, P. Fischer, W. Frey, Tetrahedron 2003, 59, 3769-3778.
55. J. Christoffers, T. Werner, S. Unger, W. Frey, Eur. J. Org. Chem. 2003, 425-431.
56. a) J. Christoffers, B. Kreidler, H. Oertling, S. Unger, W. Frey, Synlett 2003, 493-496;
57. b) J. Christoffers, B. Kreidler, S. Unger, W. Frey, Eur. J. Org. Chem. 2003, DOI 10.1002/EJOC.200300191.