Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions

Angewandte Chemie - International Edition

Volumn 42, Issue 15, 2003, Pages 1688-1690

  Christoffers, Jens ^a   Baro, Angelika ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Asymmetric catalysis; C C coupling; Enantioselectivity; Michael addition; Transition metals

Indexed keywords

PALLADIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

QUATERNARY STEREOCENTERS;

STEREOCHEMISTRY;

COBALT; LIGAND; PALLADIUM; RHODIUM; TRANSITION ELEMENT;

ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COVALENT BOND; ENANTIOSELECTIVITY; MICHAEL ADDITION; QUATERNARY; SHORT SURVEY; STEREOCHEMISTRY; SUBSTITUTION REACTION; TERTIARY;

EID: 0037541354     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200201614     Document Type: Short Survey

References (50)

1. a) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597;
2. a) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597;
3. b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401;
4. b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401;
5. c) K. Fuji, Chem. Rev. 1993, 93, 2037-2066;
6. d) S. F. Martin, Tetrahedron 1980, 36, 419-460.
7. a) E. D. Bergmann, D. Ginsburg, R. Pappo, Org. React. 1959, 10, 179-555;
8. b) D. A. Oare, C. H. Heathcock in Topics in Stereochemistry, Vol. 19 (Eds.: E. L. Eliel, S. H. Wilen), Wiley-Interscience, New York, 1989, pp. 227-407;
9. c) Tetrahedron Organic Chemistry Series, Vol. 9: P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992;
10. d) For intramolecular Michael reactions, see: R. D. Little, M. R. Masjedizadeh, O. Wallquist, J. I. McLoughlin, Org. React. 1995, 47, 315-552.
11. J. Christoffers, Eur. J. Org. Chem. 1998, 1259-1266.
12. a) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171-196;
13. b) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061;
14. c) J. Leonard, E. Díez-Barra, S. Merino, Eur J. Org. Chem. 1998, 2051-2061;
15. d) Y. Yamamoto, S. G. Pyne, D. Schinzer, B. L. Feringa, J. F. G. A. Jansen, Methoden Org. Chem. (Houben-Weyl), 4th ed. 1952-, Vol. E21b, 1995, pp. 2011-2155;
16. e) B. E. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 771-806.
17. Y. Hamashima, D. Hotta, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 11240-11241.
18. a) H. Wynberg, R. Helder, Tetrahedron Lett. 1975, 4057-4060;
19. b) K. Hermann, H. Wynberg, Helv. Chim. Acta 1977, 60, 2208-2212.
20. H. Brunner, B. Hammer, Angew. Chem. 1984, 96, 305-306; Angew. Chem. Int. Ed. Engl. 1984, 23, 312-313.
21. H. Brunner, B. Hammer, Angew. Chem. 1984, 96, 305-306; Angew. Chem. Int. Ed. Engl. 1984, 23, 312-313.
22. a) G. Desimoni, P. Quadrelli, P. P. Righetti, Tetrahedron 1990, 46, 2927-2934;
23. b) G. Desimoni, G. Dusi, G. Faita, P. Quadrelli, P. P. Righetti, Tetrahedron 1995, 51, 4131-4144;
24. c) G. Desimoni, G. Faita, S. Filippone, M. Mella, M. G. Zampori, M. Zema, Tetrahedron 2001, 57, 10203-10212.
25. a) M. Sawamura, H. Hamashima, Y. Ito, Tetrahedron: Asymmetry 1991, 2, 593-596;
26. b) M. Sawamura, H. Hamashima, Y. Ito, J. Am. Chem. Soc. 1992, 114, 8295-8296;
27. c) M. Sawamura, H. Hamashima, Y. Ito, Tetrahedron 1994, 50, 4439-4454;
28. d) M. Sawamura, H. Hamashima, H. Shinoto, Y. Ito, Tetrahedron Lett. 1995, 36, 6479-6482;
29. e) M. Sawamura, H. Hamashima, Y. Ito, Bull. Chem. Soc. Jpn. 2000, 73, 2559-2562.
30. Y. Motoyama, Y. Koga, K. Kobayashi, K. Aoki, H. Nishiyama, Chem. Eur. J. 2002, 8, 2968-2975.
31. a) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187-2209;
32. b) M. Kanai, M. Shibasaki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, Weinheim, 2000, pp. 569-592.
33. Y. Xu, K. Ohori, T. Ohshima, M. Shibasaki, Tetrahedron 2002, 58, 2585-2588.
34. H. Sasai, E. Emori, T. Arai, M. Shibasaki, Tetrahedron Lett. 1996, 37, 5561-5564.
35. Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506-6507.
36. a) S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473-8478;
37. b) N. Kumagai, S. Matsunaga, M. Shibasaki, Org. Lett. 2001, 3, 4251-4254;
38. c) R. Takita, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2002, 43, 4661-4665;
39. d) S. Matsunaga, T Ohshima, M. Shibasaki, Adv. Synth. Catal. 2002, 344, 3-15;
40. e) M. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun. 2002, 1989-1999.
41. S. Harada, N. Kumagai, T. Kinoshita, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2582-2590.
42. a) M. Pfau, G. Revial, A. Guingant, J. d'Angelo, J. Am. Chem. Soc. 1985, 107, 273-274;
43. b) I. Jabin, G. Revial, M. Pfau, P. Netchitaïlo, Tetrahedron: Asymmetry 2002, 13, 563-567;
44. c) C. Camara, D. Joseph, F. Dumas, J. d'Angelo, A. Chiaroni, Tetrahedron Lett. 2002, 43, 1445-1448;
45. d) J. d'Angelo, D. Desmaäle, F. Dumas, A. Guingant, Tetrahedron: Asymmetry 1992, 3, 459-505.
46. L. Keller, C. Camara, A. Pinheiro, F. Dumas, J. D'Angelo, Tetrahedron Lett. 2001, 42, 381-383.
47. a) J. Christoffers, A. Mann, Angew. Chem. 2000, 112, 2871-2874; Angew. Chem. Int. Ed. 2000, 39, 2752-2754;
48. a) J. Christoffers, A. Mann, Angew. Chem. 2000, 112, 2871-2874; Angew. Chem. Int. Ed. 2000, 39, 2752-2754;
49. b) J. Christoffers, A. Mann, Chem. Eur. J. 2001, 7, 1014-1027.
50. J. Christoffers, H. Scharl, Eur. J. Org. Chem. 2002, 1505-1508.