Synthesis of novel chiral phosphines from α,α-trehalose

Tetrahedron Asymmetry

Volumn 10, Issue 20, 1999, Pages 4029-4035

  Yonehara, Koji ^a   Hashizume, Tomohiro ^a   Ohe, Kouichi ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE DERIVATIVE; TREHALOSE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0033407482     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00430-9     Document Type: Article

References (34)

1. For recent overviews, see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. (b) Ojima, I. Asymmetric Synthesis; Verlag: New York, 1993.
2. For recent overviews, see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. (b) Ojima, I. Asymmetric Synthesis; Verlag: New York, 1993.
3. (a) RajanBabu, T. V.; Radetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429.
4. (b) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. Chem. Commun. 1999, 415.
5. (c) Boog-Wick, K.; Pregosin, P. S.; Wörle, M.; Albinati, A. Helv. Chim. Acta 1998, 81, 1622.
6. (d) Gläser, B.; Kunz, H. Synlett 1998, 53.
7. (e) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012.
8. (f) Selke, R.; Ohff, M.; Riepe, A. Tetrahedron 1996, 52, 15079.
9. (g) Berens, U.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 2055.
10. (h) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869.
11. (i) Selke, R.; Facklam, C.; Foken, H.; Heller, D. Tetrahedron: Asymmetry 1993, 4, 369.
12. (j) Selke, R. J. Organomet. Chem. 1989, 370, 249.
13. (k) Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213.
14. (l) Yamashita, M.; Hiramatsu, K.; Yamada, M.; Suzuki, N.; Inokawa, S. Bull. Chem. Soc. Jpn. 1982, 55, 2917.
15. (m) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62.
16. (n) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29.
17. (o) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635.
18. Brown, M. A.; Cox, P. J.; Howie, R. A.; Melvin, O. A.; Taylor, O. J.; Wardell, J. L. J. Organomet. Chem. 1995, 498, 275.
19. Shi, J.-C.; Hong, M.-C.; Wu, D.-X.; Liu, Q.-T.; Kang, B.-S. Chem. Lett. 1995, 685.
20. (a) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Adv. Catal. Proc. 1997, 2, 1.
21. (b) Gilbertson, S. R.; Chang, C.-W.T. J. Org. Chem. 1995, 60, 6226.
22. (c) Brown, J. M.; Cook, S. J.; Khan, R. Tetrahedron 1986, 42, 5105.
23. Yonehara, K.; Hashizume, T.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1998, 71, 1967.
24. Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593.
25. For an overview, see: Holz, J.; QuirmBach, M.; Börner, A. Synthesis 1997, 983, and references cited therein.
26. Baer, H. H.; Radatus, B. Carbohydr. Res. 1984, 128, 165.
27. Hough, L.; Munroe, P. A.; Richardson, A. C. J. Chem. Soc. (C) 1971, 1090.
28. Greene T. A.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd Ed.; John Wiley: New York, 1991.
29. (a) De Belder, A. N. Adv. in Carbohydr. Chem. Biochem. 1977, 34, 179.
30. (b) De Belder, A. N. Adv. in Carbohydr. Chem. 1965, 20, 219.
31. Wallace, P. A.; Minnikin, D. E. Carbohydr. Res. 1994, 263, 43.
32. Van Rijsbergen, R.; Anteunis, M. J. O.; De Bruyn, A. J. Carbohydr. Chem. 1983, 2, 395.
33. At present we cannot rule out the possibility that the complex 12 contains a two phosphine ligands bridge between two rhodium metal centers (Rh:ligand=2:2). The unambiguous structure of 12 has not yet been clarified.
34. Hydrogenation of methyl α-acetamidocinnamate in MeOH using the rhodium complex 12 gave the (S)-hydrogenated product with 12% ee.