Chiral amino alcohols bound to diimines, diamines and dendrimers as chiral ligands for the enantioselective ethylation of N-diphemylphosphinylimines

Tetrahedron Asymmetry

Volumn 8, Issue 24, 1997, Pages 4033-4040

  Suzuki, Takefumi ^a   Hirokawa, Yutaka ^a   Ohtake, Koji ^a   Shibata, Takanori ^a   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; EPHEDRINE DERIVATIVE; PHOSPHINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031584590     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00553-3     Document Type: Article

References (37)

1. (a) D. A. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder and P. Smith, Polym. Journal, 1985, 17, 117;
2. (b) D. A. Tomalia, A. M. Naylor and W. A. Goddard III, Angew. Chem. Int. Ed. Engl, 1990, 29, 138;
3. (c) D. A. Tomalia, Aldrichim. Acta, 1993, 26, 91;
4. (d) J. Issberner, R. Moors and F. Vögtle, Angew. Chem. Int. Ed. Engl., 1994, 33, 2413;
5. (e) J. Issberner, M. Böhme, S. Grimme, M. Nieger, W. Paulus and F. Vögtle, Tetrahedron: Asymmetry, 1996, 7, 2223;
6. (f) G. R. Newkome, C. N. Moorefield and G. R. Baker, Aldrichim. Acta, 1992, 25, 31 ;
7. (g) J. M. J. Fréchet, Science, 1994, 263, 1710;
8. (h) J. W. J. Knapen, A. W. van der Made, J. C. de Wilde, P. W. N. M. van Leeuwen, P. Wljkens, D. M. Grove and G. van Koten, Nature, 1994, 372, 639.
9. (a) D. Seebach, J.-M. Lapierre, K. Skobridis and G. Greiveldinger, Angew. Chem. Int. Ed. Engl., 1994, 33, 440;
10. (b) D. Seebach, J.-M. Lapierre, G. Greiveldinger and K. Skobridis, Helv. Chim. Acta, 1994, 77, 1673;
11. (c) J. A. Kremers and E. W. Meijer, J. Org. Chem., 1994, 59, 4262;
12. (d) H.-F. Chow, L. F. Fok and C. C. Mak, Tetrahedron Lett., 1994, 35, 3547;
13. (e) L. J. Twyman, A. E. Beezer and J. C. Mitchell, Tetrahedron Lett., 1994, 35, 4423;
14. (f) H. Brunner and P. Bublak, Synthesis, 1995, 36.
15. (a) H. Brunner, J. Organomet. Chem., 1995, 500, 39;
16. (b) H. Brunner and S. Altmann, Chem. Ber., 1994. 127, 2285;
17. (c) H. Brunner and J. Fürst, Tetrahedron, 1994, 50, 4303;
18. (d) H. Brunner and G. Net, Synthesis, 1995, 423;
19. (e) C. Bolm, N. Derrien and A. Seger, Synlett., 1996, 387;
20. (f) D. Seebach, R. E. Marit and T. Hintermann, Helv. Chim. Acta, 1996, 79, 1710.
21. (a) K. Soai, T. Hatanaka and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097;
22. (b) T. Hayase, Y. Inoue, T. Shibata and K. Soai, Tetrahedron: Asymmetry, 1996, 7, 2509.
23. (a) K. Soai, T. Suzuki and T. Shono, T. J. Chem. Soc., Chem. Commun., 1994, 317;
24. (b) T. Suzuki, N. Narisada, T. Shibata and K. Soai, Tetrahedron: Asymmetry, 1996, 7, 2519;
25. (c) T. Suzuki, T. Shibata and K. Soai, J. Chem. Soc., Perkin Trans. 1, 1997, 2757.
26. Reviews, (a) K. Soai and T. Hayase, Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn), 1995. 59, 138;
27. (b) K. Soai and T. Shibata, Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn), in press;
28. (c) cf. K. Soai and S. Niwa, Chem. Rev., 1992, 92, 833;
29. (d) cf. R. Noyori and M. Kitamura, Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
30. For the use of a chiral diamino diol in the enantioselective alkylation of aldehydes, see K. Soai, M. Nishi and Y. Ito, Chem. Lett., 1987, 2405.
31. R. Ramage, D. Hopton, M. J. Parrott, G. W. Kenner and G. A. Moore, J. Chem. Soc., Perkin Trans. 1, 1984, 1357.
32. For the enantioselective alkylation of imines by other groups, (a) I. Inoue, M. Shindo, K. Koga, M. Kanai and K. Tomioka, Tetrahedron: Asymmetry, 1996, 6, 2527;
33. (b) M. Nakamura, A. Hirai and E. Nakamura, J. Am. Chem. Soc, 1996, 118, 8489;
34. (c) S. E. Denmark, N. Nakajima and O. J.-C. Nicaise, J. Am. Chem. Soc., 1994, 116, 8797;
35. (d) S. Itsuno, H. Yanaka, C. Hachisuka and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 3095;
36. (e) A. R. Katritzky and P. A. Harris, Tetrahedron: Asymmetry, 1992, 3, 437.
37. W. B. Jennings and C. J. Lovely, Tetrahedron, 1991, 47, 5561.