Organotransition metal modified sugars 14. Activation of sugar-based alkynols at a metal carbonyl template: A metal vinyl carbene functionalization of carbohydrates and non-conventional route to organometallic disaccharides

Journal of Organometallic Chemistry

Volumn 589, Issue 1, 1999, Pages 11-20

  Dötz, Karl Heinz ^a   Paetsch, Daphne ^a   Le Bozec, Hubert ^b  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

Carbene complexes; Carbohydrates; Diels Alder Reactions; Disaccharides

Indexed keywords

EID: 0039116381     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(99)00295-8     Document Type: Article

References (36)

1. Haase W.-C., Nieger M., Dötz K.H. Chem. Eur. J. 5:1999;2014.
2. E.O. Fischer, A. Maasböl, Angew. Chem. 76 (1964) 645; Angew. Chem. Int. Ed. Engl. 3 (1964) 580.
3. E.O. Fischer, A. Maasböl, Angew. Chem. 76 (1964) 645; Angew. Chem. Int. Ed. Engl. 3 (1964) 580.
4. Reviews: (a) K.H. Dötz, Angew. Chem. 96 (1984) 573; Angew. Chem. Int. Ed. Engl. 23 (1984) 587. (b) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, New York, 1995, pp. 469-547. (c) D.F. Harvey, D.M. Sigano, Chem. Rev. 96 (1996) 271. (d) A. Meijere, Pure Appl. Chem. 68 (1996) 61.
5. Reviews: (a) K.H. Dötz, Angew. Chem. 96 (1984) 573; Angew. Chem. Int. Ed. Engl. 23 (1984) 587. (b) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, New York, 1995, pp. 469-547. (c) D.F. Harvey, D.M. Sigano, Chem. Rev. 96 (1996) 271. (d) A. Meijere, Pure Appl. Chem. 68 (1996) 61.
6. Reviews: (a) K.H. Dötz, Angew. Chem. 96 (1984) 573; Angew. Chem. Int. Ed. Engl. 23 (1984) 587. (b) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, New York, 1995, pp. 469-547. (c) D.F. Harvey, D.M. Sigano, Chem. Rev. 96 (1996) 271. (d) A. Meijere, Pure Appl. Chem. 68 (1996) 61.
7. Reviews: (a) K.H. Dötz, Angew. Chem. 96 (1984) 573; Angew. Chem. Int. Ed. Engl. 23 (1984) 587. (b) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, New York, 1995, pp. 469-547. (c) D.F. Harvey, D.M. Sigano, Chem. Rev. 96 (1996) 271. (d) A. Meijere, Pure Appl. Chem. 68 (1996) 61.
8. Reviews: (a) K.H. Dötz, Angew. Chem. 96 (1984) 573; Angew. Chem. Int. Ed. Engl. 23 (1984) 587. (b) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, New York, 1995, pp. 469-547. (c) D.F. Harvey, D.M. Sigano, Chem. Rev. 96 (1996) 271. (d) A. Meijere, Pure Appl. Chem. 68 (1996) 61.
9. (a) W.D. Wulff, B.A. Anderson, A.J. Toole, Y.-C. Xu, Inorg. Chim. Acta 220 (1994) 215.
10. (b) Y.-C. Anderson, W.D. Wulff, A.J. Rahm, Am. Chem. Soc. 115 (1993) 4602.
11. (c) J. Barluenga, J.M. Montserrat, J. Florez, S. Gracia-Granda, E. Martin, Chem. Eur. J. 1 (1995) 236.
12. Review: L.S. Hegedus, Tetrahedron 53 (1997) 4105.
13. (a) W.D. Wulff, W.E. Bauta, R.W. Kaesler, P.J. Lankford, R.A. Miller, C.K. Murray, D.C. Yang, J. Am. Chem. Soc. 112 (1990) 3642.
14. (b) W.D. Wulff, T.S. Powers, J. Org. Chem. 58 (1993) 2381.
15. Reviews: (a) S. Hanessian, Preparative Carbohydrate Chemistry, Marcel Dekker, New York, 1997. (b) S.H. Khan, R.A. O'Neill, Modern Methods in Carbohydrate Synthesis, Overseas Publishers Association, Amsterdam, 1996. (c) M.H.D. Postema, C-Glycoside Synthesis, CRC Press, Boca Raton, 1995. (d) I. Frappa, D. Sinou, J. Carbohydr. Chem. 16 (1997) 255. (e) K.H. Dötz, R. Ehlenz, Chem. Eur. J. 3 (1997) 1751.
16. Reviews: (a) S. Hanessian, Preparative Carbohydrate Chemistry, Marcel Dekker, New York, 1997. (b) S.H. Khan, R.A. O'Neill, Modern Methods in Carbohydrate Synthesis, Overseas Publishers Association, Amsterdam, 1996. (c) M.H.D. Postema, C-Glycoside Synthesis, CRC Press, Boca Raton, 1995. (d) I. Frappa, D. Sinou, J. Carbohydr. Chem. 16 (1997) 255. (e) K.H. Dötz, R. Ehlenz, Chem. Eur. J. 3 (1997) 1751.
17. Reviews: (a) S. Hanessian, Preparative Carbohydrate Chemistry, Marcel Dekker, New York, 1997. (b) S.H. Khan, R.A. O'Neill, Modern Methods in Carbohydrate Synthesis, Overseas Publishers Association, Amsterdam, 1996. (c) M.H.D. Postema, C-Glycoside Synthesis, CRC Press, Boca Raton, 1995. (d) I. Frappa, D. Sinou, J. Carbohydr. Chem. 16 (1997) 255. (e) K.H. Dötz, R. Ehlenz, Chem. Eur. J. 3 (1997) 1751.
18. Reviews: (a) S. Hanessian, Preparative Carbohydrate Chemistry, Marcel Dekker, New York, 1997. (b) S.H. Khan, R.A. O'Neill, Modern Methods in Carbohydrate Synthesis, Overseas Publishers Association, Amsterdam, 1996. (c) M.H.D. Postema, C-Glycoside Synthesis, CRC Press, Boca Raton, 1995. (d) I. Frappa, D. Sinou, J. Carbohydr. Chem. 16 (1997) 255. (e) K.H. Dötz, R. Ehlenz, Chem. Eur. J. 3 (1997) 1751.
19. Reviews: (a) S. Hanessian, Preparative Carbohydrate Chemistry, Marcel Dekker, New York, 1997. (b) S.H. Khan, R.A. O'Neill, Modern Methods in Carbohydrate Synthesis, Overseas Publishers Association, Amsterdam, 1996. (c) M.H.D. Postema, C-Glycoside Synthesis, CRC Press, Boca Raton, 1995. (d) I. Frappa, D. Sinou, J. Carbohydr. Chem. 16 (1997) 255. (e) K.H. Dötz, R. Ehlenz, Chem. Eur. J. 3 (1997) 1751.
20. (a) D. Paetsch, K. H. Dötz, Tetrahedron Lett. 40 (1999) 487.
21. (b) M. Klumpe, K.H. Dötz, Chem. Eur. J. 5 (1999) 691.
22. (a) K.H. Dötz, O. Neuß, M. Nieger, Synlett (1996) 995.
23. (b) K.H. Dötz, R. Ehlenz, O. Neuß, M. Teckenbrock, Tetrahedron 53 (1997) 5143.
24. (c) B. Weyershausen, M. Nieger, K.H. Dötz, Organometallics 17 (1998) 1602.
25. (a) M. Bruce, G. Swincer, B.J. Thompson, R.C. Wallis, Aust. J. Chem. 33 (1980) 2605.
26. (b) K.H. Dötz, W. Sturm, H.G. Alt, Organometallics 6 (1987) 1424.
27. (c) F.E. McDonald, M.M. Gleason, Angew. Chem. 107 (1995) 356; Angew. Chem. Int. Ed. Engl. 44 (1995) 350.
28. (c) F.E. McDonald, M.M. Gleason, Angew. Chem. 107 (1995) 356; Angew. Chem. Int. Ed. Engl. 44 (1995) 350.
29. (a) H. Le Bozec, C. Cosset, P.H. Dixneuf, J. Chem. Soc. Chem. Commun. (1991) 881.
30. (b) C. Cosset, I. Del Rio, H. Le Bozec, Organometallics 14 (1995) 1939.
31. According to: G.A. Kraus, M.T. Molina, J. Org. Chem. 53 (1988) 753.
32. Horton D., Koh D. Carbohydr. Res. 250:1993;249.
33. The perbenzylated arabinose and ribose were prepared by thioacetalization of the unprotected sugars: (a) J.C. Roberts, H.T. Nagasawa, R.T. Zera, R.F. Fricke, D.J.W. Goon, J. Med. Chem. 30 (1987) 1891; followed by benzylation: (b) A. Dondoni, A. Marra, P. Merino, J. Am. Chem. Soc. 116 (1994) 3324; and dethioacetalization: (c) V. Poszgay, H.J. Jennings, J. Org. Chem. 53 (1988) 4042. (d) The carbonyl precursors of 7 and 9 were obtained according to: S. Hanessian, U. Ugolini, Carbohydr. Res. 130 (1984) 261; by oxidation of the unprotected OH group with PCC.
34. The perbenzylated arabinose and ribose were prepared by thioacetalization of the unprotected sugars: (a) J.C. Roberts, H.T. Nagasawa, R.T. Zera, R.F. Fricke, D.J.W. Goon, J. Med. Chem. 30 (1987) 1891; followed by benzylation: (b) A. Dondoni, A. Marra, P. Merino, J. Am. Chem. Soc. 116 (1994) 3324; and dethioacetalization: (c) V. Poszgay, H.J. Jennings, J. Org. Chem. 53 (1988) 4042. (d) The carbonyl precursors of 7 and 9 were obtained according to: S. Hanessian, U. Ugolini, Carbohydr. Res. 130 (1984) 261; by oxidation of the unprotected OH group with PCC.
35. The perbenzylated arabinose and ribose were prepared by thioacetalization of the unprotected sugars: (a) J.C. Roberts, H.T. Nagasawa, R.T. Zera, R.F. Fricke, D.J.W. Goon, J. Med. Chem. 30 (1987) 1891; followed by benzylation: (b) A. Dondoni, A. Marra, P. Merino, J. Am. Chem. Soc. 116 (1994) 3324; and dethioacetalization: (c) V. Poszgay, H.J. Jennings, J. Org. Chem. 53 (1988) 4042. (d) The carbonyl precursors of 7 and 9 were obtained according to: S. Hanessian, U. Ugolini, Carbohydr. Res. 130 (1984) 261; by oxidation of the unprotected OH group with PCC.
36. The perbenzylated arabinose and ribose were prepared by thioacetalization of the unprotected sugars: (a) J.C. Roberts, H.T. Nagasawa, R.T. Zera, R.F. Fricke, D.J.W. Goon, J. Med. Chem. 30 (1987) 1891; followed by benzylation: (b) A. Dondoni, A. Marra, P. Merino, J. Am. Chem. Soc. 116 (1994) 3324; and dethioacetalization: (c) V. Poszgay, H.J. Jennings, J. Org. Chem. 53 (1988) 4042. (d) The carbonyl precursors of 7 and 9 were obtained according to: S. Hanessian, U. Ugolini, Carbohydr. Res. 130 (1984) 261; by oxidation of the unprotected OH group with PCC.