Hydroxyalkylation of Lithiated 3-[(S)-2(Methoxymethy)pyrrolidino]- 1,3-diphenylpropene - an Asymmetric Homoaldol Reaction - an

Chemische Berichte

Volumn 129, Issue 10, 1996, Pages 1161-1168

  Ahlbrecht, Hubertus ^a   Kramer, Andreas ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

1 aminoally! anions, chiral; Acetoxy ketones, chiral; Homoaldol reaction, chiral; Homoenolate equivalents, chiral; Hydroxyalkylation

Indexed keywords

EID: 0000485792     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19961291004     Document Type: Article

References (64)

1. [1a] A. Kramer, Diplomarbeit, University of Gieen, 1990.
2. [1b| A. Kramer, Dissertation, University of Gießen, 1995.
3. [2a] Q_ zimmermann, Dissertation, University of Gießen, 1985.
4. [2b] H. Ahlbrecht, D. Enders, L. Santowski, G. Zimmermann, Chem. Ber. 1989, 122, 1995-2004.
5. [2c] L. Santowski, Dissertation, University of Gieen, 1992.
6. [3a], H. Sommer, Diplomarbeit, University of Gießen, 1986.
7. [3b] H. Sommer. Dissertation. University of Gießen, 1990.
8. [3c] H. Ahlbrecht, H. Sommer, Chem. Ber. 1990, 123, 829-836.
9. Review: D. Hoppe, Angew. Chem. 1984, 96, 930-946;
10. Angew. Chem. Int. Ed. Engt 1984, 23, 932.
11. [5a] V. J. Jephcote, A. J. Pratt, E. J. Thomas, J. Chem. Soc., Chem. Commun. 1984, 800-802.
12. [5b] V. J. Jephcote, A. J. Pratt, E. I Thomas, J. Chem. Soc., Chem. Commun. 1989, 1521-1527;
13. J. Chem. Soc., Perkin Trans. /, 1989, 1529-1535.
14. [5c] B. W. Gung, D. T. Smith, M. A. Wolf, Tetrahedron Lett. 1991, 32, 13- 16
15. [5d] B. W. Gung, A. J. Peat. B. M. Snook, D. T. Smith, Tetrahedron Leu. 1991, 32 453-456.
16. [5e] J. A. Marshall, D. M. Yashunsky, J. Org. Chem. 1991, 56, 5493-5495.
17. - I5'1 P. Bravo, P. Carrera, G. Resnati, C. Ticozzi, J. Chem. Soc. Chem. Commun. 1984, 19-20.
18. [5f] H. Roder, G. Heimchen, E. Peters, K. Peters, H. v. Sehnering, Angew. Chem. 1984, 96, 895-898.
19. [5g] S. Kano, T. Yokomatsu, S. Shibuya, Tetrahedron Leu. 1991, 32, 233-236.
20. [5i] H. Gais, H. Müllen l Decker, R. Mainz, Tetrahedron Lett. 1995, 36, 7433-7436.
21. [5j] P. Beak, H. Du, J. Arn. Chem. Soc. 1993, 115, 2516-2518.
22. [6 [6a] T. Krämer, D. Hoppe, Tetrahedron Lett. 1987, 28, 5149-5152.
23. [6b] D. Hoppe, T. Krämer, J. Schwark, O. Zschage, Pure Aopl. Chem. 1990, 62, 1999-2006.
24. [7al D. Hoppe, Ö. Zschage, Angew. Chem. 1989, 101, 67-69;
25. Angew. Chem. Int. Ed. Engl. 1989, 28, 69.
26. [7b] O. Zschage, D. Hoppe, Tetrahedron 1992, 48, 5657-5666.
27. [sa] H. Ahlbrecht, G. Rauchschwalbe, Synthesis 1973, 417-420.
28. [8b] G. Rauchschwalbe, Dissertation, university of Gießen, 1974.
29. [8c] G. Rauchschwalbe, H. Ahlbrecht, Svnthesis 1974, 663-665.
30. C. Sannen Diplomarbeit, University of Gießen, 1985.
31. [lü| H. O. Kalinowski, S. Berger, S. Braun. "C-NMR-Spektroskopie, Georg Thieme Verlag, Stuttgart, 1984, p. 264.
32. [11a] S. Massmune. S. A. All. D. L. Snitman, D. S. Garvey, Angew. Chem. 1980, 92, 573-575;
33. Chem. Im. Ed. Eng!. 1980, 19, 557.
34. [11b] S. Masamune, T. Kaino, D. S. Garvey, J. Am. Chem. Soc. 1982, 104, 5521-5523.
35. [11c] D. Seebech, V. Prelog. Ançew. Chem. 1982. 94. 696-702:
36. Augen: Chem. In;. ^ Ed. Engl. 1982, 21, 654.
37. About the influence of Li+ on the reactivity of carbonyi compounds see:
38. [2a] J. L. Pierre, H. Hände!, R. Perraud. Tetrahedron 1975, 31, 2795-2798.
39. [12b] H. Handel, J. L. Pierre, Te:ruhedron 1975, 31, 2799-2802.
40. [12c]: H. Handel, J. L. Pierre, Tetrahedron Lett. 1976, 2029-2032.
41. [12d] A. Loupy, J. Seyden-Penne, P. Tchoubar, Tetrahedron Lett. 1976, 1677-1680.
42. [12e] O. Eisenstein, J. M. Lefour, C. Minen, Tetrahedron Lett. 1976, 1681-1684.
43. H. O. House, D. S. Crumrine, A. Y. Teranishi, H. D. Olmstead, J. Am. Chem. Soc. 1973, 95, 3310-3324.
44. D. Hoppe, R. Manko, A. Brönneke, F. Lichtenbcrg, E. v. Hülsen, Chem. Ber. 1985, 118, 2822-2851.
45. [15a] T j Leitereg, D. J. Cram, J. Am. Chem. Soc. 1968, 90, 4011-4018.
46. [15b] T. Imamoto, T. Mukaiyama, Chem. Lett. 1980, 45-46.
47. [15c] K. Soai, T. Hayasaka, S. üsajin, S. Yokoy-ama, Chem. Lett. 1988, 1571-1572.
48. D. H. R. Barton, W. B. Motherwell, Pure Apnl. Chem. 1981, 53. 15-31.
49. W. Hartwig, Tetrahedron 1983, 39, 2609-2645.
50. D. H. R. Barton, S. W. McCombie, J. Chem. Soc., Perk'm Trans. 1. 1975. 1574-15S5.
51. K. Nozaki, K. Oshima, K. Utimoto, Bull. Chem. Soc. Jnn. 1990, 63, 2578-2583.
52. M. Ballestri, C. Chatgilialoglu, K. B. Clark, D. Griiler, B. Giese, B. Kopping, J. Org. Chem. 1991, 56, 678-683.
53. D. Schummer, G. Hölle, Svnleit 1990, 705-706.
54. H. AhlbrechL, G. Boche, K. Harms. VI. Marsch, H. Sommer, Chem. Ber. 1990, 123, 1853-1858.
55. £ia| R. \y Hoffmann, Ançew. Chem. 1982, 94, 569-580;
56. Angen: Chem. In!. Ed. Engl. 1982. 21, 555.
57. [23b] Y. Yamamoto. K. Marujama, Heierocvcles 1982, 18, 357-386.
58. R. Gompper, H.-U.'Wagner, Angew. Chem. 1976, 118, 389-401;
59. Angev.:. Chem. Int. Ed. Eng!. 1976, 75, 321.
60. W. G. Kofron, M. Baclawski. J. Org. Chem. 1976, 41, . 1879-1880.
61. [26a] ^ Xützel in Methoden der organischen Chemie 'Houben-Weyl), vol. XIII/2a, Georg Thieme Verlag, Stuttgart, 1973, p. 54.
62. [26b] Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin, 1977, p. 623.
63. G. Dana, A. Zysman, Bull. Soc. Chirn. Fr. 1975, 1951-1956.
64. J. E. Leibner, J. Jacobus, J. Org. Chem. 1979, 44, 449-450.