Synthesis of C2-symmetrical chiral diamines: Diastereoselective addition to bis(1,3-oxazolidinyl)alkanes with Grignard reagents

Tetrahedron Asymmetry

Volumn 11, Issue 14, 2000, Pages 3003-3015

  Yamauchi, Takayasu ^a   Higashiyama, Kimio ^a   Kubo, Hajime ^a   Ohmiya, Shigeru ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; DIAMINE;

ARTICLE; CHEMICAL ANALYSIS; CHIRALITY; CRYSTALLOGRAPHY; PRIORITY JOURNAL; STEREOISOMERISM; SYNTHESIS;

EID: 0034725606     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00268-8     Document Type: Article

References (75)

1. (a) Pasini, A.; Zunino, F. Angew. Chem. 1987, 99, 632; Angew. Chem., Int. Ed. Engl. 1987, 26, 615;
2. (a) Pasini, A.; Zunino, F. Angew. Chem. 1987, 99, 632; Angew. Chem., Int. Ed. Engl. 1987, 26, 615;
3. (b) Brunner, H.; Hankofer, P.; Holzinger, U.; Treittinger, B.; Schönenberger, H. Eur. J. Med. Chem. 1990, 25, 35;
4. (c) Brunner, H.; Hankofer, P.; Holzinger, U.; Treittinger, B. Chem. Ber. 1990, 123, 1029;
5. (d) Gust, R.; Burgemeister, T.; Mannschreck, A.; Schönenberger, H. J. Med. Chem. 1990, 33, 2535;
6. (e) Kelland, L. R.; Abel, G.; McKeage, M. J.; Jones, M.; Goddard, P. M.; Valenti, M.; Murrer, B. A.; Harrap, K. R. Cancer Res. 1993, 53, 2581;
7. (f) Kim, D.-K.; Kim, Y.-W.; Kim, H.-T.; Kim, K. H. Bioorg. Med. Chem. Lett. 1996, 6, 643;
8. (g) Reedijk, J. Chem. Commun. 1996, 801;
9. (h) Khokhar, A. R.; Al-Baker, S.; Shamsuddin, S.; Siddik, Z. H. Bioorg. Med. Chem. Lett. 1997, 40, 112.
10. (a) Kanemasa, S.; Hamura, S.; Harada, E.; Yamamoto, H. Tetrahedron Lett. 1994, 35, 7985;
11. (b) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264;
12. (c) Saito, T.; Takekawa, K.; Takahashi, T. Chem. Commum. 1999, 1001.
13. Song, J.-H.; Cho, D.-J.; Jeon, S.-J.; Kim, Y.-H.; Kim, T.-J.; Jeong, J. H. Inorg. Chem. 1999, 38, 893.
14. Tomioka, K.; Nakajima, M.; Iitaka, Y.; Koga, K. Tetrahedron Lett. 1988, 29, 573.
15. Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135.
16. (a) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897;
17. (b) Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705;
18. (c) Pertici, P.; D'Arata, F.; Rosini, C. j. Organomet. Chem. 1996, 515.
19. Gao, J.-X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087.
20. Santi, C.; Fragale, G.; Wirth, Tetrahedron: Asymmetry 1998, 9, 3625.
21. (a) Gawley, R. E.; Aube', J. In Principles of Asymmetric Synthesis; Pergamon Press: Oxford, 1996;
22. (b) Ikeda, M.; Hirano, T.; Tsuruta, T. Tetrahedron Lett. 1972, 4977;
23. (c) Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321;
24. (d) Daly, A. M.; Dalton, C. T.; Renehan, M. F.; Gilheany, D. G. Tetrahedron Lett. 1999, 40, 3617.
25. (a) Gravert, D. J.; Griffin, J. H. J. Org. Chem. 1993, 55, 820;
26. (b) Sato, K.; Chikira, M.; Fujii, Y.; Komatsu, A. J. Chem. Soc., Chem. Commun. 1994, 625;
27. (c) Burrows, C. J.; Rokita, S. E. Acc. Chem. Res. 1994, 27, 295;
28. (d) Bhattacharya, S. S.; Manddal, S. J. Chem. Soc., Chem. Commun. 1995, 2489;
29. (e) Gravert, D. J.; Griffin, J. H. Inorg. Chem. 1996, 35, 4837;
30. (f) Routier, S.; Bernier, J.-L.; Waring, M. J.; Colson, P.; Bailly, C. J. Org. Chem. 1996, 61, 2326;
31. (g) Tanaka, T.; Tsurutani, K.; Komatsu, A.; Ito, T.; Iida, K.; Fujii, Y.; Nakano, Y.; Usui, Y.; Fukuda, Y.; Chikira, M. Bull. Chem. Soc. Jpn. 1997, 70, 615.
32. (a) Erickson, J. W. Perspectives in Drug Discovery and Design 1993, 1, 109;
33. (b) Baker, W. R.; Condon, S. L. J. Org. Chem. 1993, 55, 3277;
34. (c) Enders, D.; Jegelka, U.; Dücker, B. Angew. Chem. 1993, 105, 423; Angew. Chem., Int. Ed. Engl. 1993, 32, 423;
35. (c) Enders, D.; Jegelka, U.; Dücker, B. Angew. Chem. 1993, 105, 423; Angew. Chem., Int. Ed. Engl. 1993, 32, 423;
36. (d) Kempf, D. J.; Codacovi, L.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Saldivar, A.; Vasavanonda, S.; Marsh, K. C.; Bryant, P.; Sham, H. L.; Green, B. E.; Betebenner, D. A.; Erickson, J.; Norbeck, D. W. J. Med. Chem. 1993, 36, 320;
37. (e) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem. 1994, 106, 719; Angew. Chem., Int. Ed. Engl. 1994, 33, 685;
38. (e) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem. 1994, 106, 719; Angew. Chem., Int. Ed. Engl. 1994, 33, 685;
39. (f) Hosur, M. V.; Bhat, T. N.; Kempf, D. J.; Baldwin, E. T.; Liu, B.; Gulnik, S.; Wideburg, N. E.; Norbeck, D. W.; Appelt, K. J.; Erickson, J. W. J. Am. Chem. Soc. 1994, 116, 847;
40. (g) Rossano, L. T.; Lo, Y. S.; Anzalone, L.; Lee, Y.-C.; Meloni, D. J.; Moore, J. R.; Gale, T. M.; Arnett, J. F. Tetrahedron Lett. 1995, 36, 4967;
41. (h) Jadhav, P. K.; Woerner, F. J. Tetrahedron Lett. 1995, 36, 6383;
42. (i) Wang, G. T.; Li, S.; Wideburg, N.; Krafft, G. A.; Kempf, D. J. J. Med. Chem. 1995, 38, 2995;
43. (j) Pierce, M. E.; Harris, G. D.; Islam, Q.; Radesca, L. A.; Storace, L.; Waltermire, R. E.; Wat, E.; Jadhav, P. K.; Emmett, G. C. J. Org. Chem. 1996, 61, 444;
44. (k) Weber, B.; Kolczewski, S.; Frohlich, R.; Hoope, D. Synthesis 1999, 1593.
45. (a) Reetz, M. T.; Jaeger, R.; Drewlies, R.; Hübel, M. Angew. Chem. 1991, 103, 76; Angew. Chem., Int. Ed. Engl. 1991, 30, 103;
46. (a) Reetz, M. T.; Jaeger, R.; Drewlies, R.; Hübel, M. Angew. Chem. 1991, 103, 76; Angew. Chem., Int. Ed. Engl. 1991, 30, 103;
47. (b) Neumann, W. L.; Rogic, M. M.; Dunn, T. J. Tetrahedron Lett. 1991, 32, 5865;
48. (c) Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391;
49. (d) Baruah, B.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1995, 36, 6747;
50. (e) Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607;
51. (f) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 36, 9241;
52. (g) Shimizu, M.; Iida, T.; Fujisawa, T. Chem. Lett. 1995, 609;
53. (h) Corey, E. J.; Lee, D.-H.; Sarshar, S. Tetrahedron: Asymmetry 1995, 6, 3;
54. (i) Bruncko, M.; Khuong, T.-A. V.; Sharpless, K. B. Angew. Chem. 1996, 108, 453; Angew. Chem., Int. Ed. Engl. 1996, 35, 454;
55. (i) Bruncko, M.; Khuong, T.-A. V.; Sharpless, K. B. Angew. Chem. 1996, 108, 453; Angew. Chem., Int. Ed. Engl. 1996, 35, 454;
56. (j) Kise, N.; Kashiwagi, K.; Watanabe, M.; Yoshida, J. J. Org. Chem. 1996, 61, 428;
57. (k) Roland, S.; Mangeney, P.; Alexakis, A. Synthesis 1999, 228.
58. (a) Denmark, S. E.; Kim, J.-H. Synthesis 1992, 229;
59. (b) Enders, D.; Meiers, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2261.
60. (a) Higashiyama, K.; Inoue, H.; Takahashi, H. Tetrahedron Lett. 1992, 33, 235;
61. (b) Higashiyama, K.; Inoue, H.; Takahashi, H. Tetrahedron 1994, 50, 1083;
62. (c) Higashiyama, K.; Inoue, H.; Yamauchi, T.; Takahashi, H. J. Chem. Soc., Perkin Trans. 1 1995, 111;
63. (d) Poerwono, H.; Higashiyama, K.; Yamauchi, T.; Takahashi, H. Heterocycles 1997, 46, 385;
64. (e) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263;
65. (f) Poerwono, H.; Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711;
66. (g) Poerwono, H.; Higashiyama, K.; Yamauchi, T.; Kubo, H.; Ohmiya, S.; Takahashi, H. Tetrahedron 1998, 54, 13955;
67. (h) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384;
68. (i) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Heterocycles 1998, 48, 1813;
69. (j) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791.
70. Takahashi, H.; Hsieh, B. C.; Higashiyama, K. Chem. Pharm. Bull. 1990, 38, 2429.
71. Mokhallalati, M. K.; Pridgen, L. N. Synth. Commun. 1993, 23, 2055.
72. 'teXsan': Crystal structure analysis package; Molecular Structure Corporation, 1985 and 1992.
73. 'SIR88': Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Polidori, G.; Spagna, R.; Viterbo, D. J. Appl. Cryst. 1989, 22, 389.
74. 'DIRDIF94': Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M. 1994. The DIRDIF-94 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands.
75. 'PATTY': Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. 1992.