A general approach to 1,2-trans-C-glycosides via glycosyl samarium(III) compounds

Chemistry - A European Journal

Volumn 4, Issue 4, 1998, Pages 655-671

  Skrydstrup, Troels ^a,c   Jarreton, Olivier ^a   Mazéas, Daniel ^b   Urban, Dominique ^a   Beau, Jean Marie ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b UNIVERSITÉ D'ORLÉANS   (France)

^c AARHUS UNIVERSITY   (Denmark)

Author keywords

C C coupling; Carbanions; Glycosides; Radicals; Samarium

Indexed keywords

EID: 0031861064     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19980416)4:4<655::aid-chem655>3.3.co;2-w     Document Type: Article

References (171)

1. a) M. H. D. Postema, C-Glycoside Synthesis, CRC Press, Boca Raton, FL, 1995;
2. b) D. E. Levy, C. Tang, The Chemistry of C-Glycosides, Pergamon, Exeter, 1995;
3. c) G. Casiraghi, F. Zanardi, G. Rassu, P. Spanu, Chem. Rev. 1995, 95, 1677;
4. d) M. H. D. Postema, Tetrahedron 1992, 48, 8545;
5. e) J. Herscovici, K. Antonakis, in Studies in Natural Product Chemistry Vol. 10(Ed.: Atta-ur-Rahman), Elsevier, Amsterdam, 1992.
6. a) T.-C. Wu, P. G. Goekjian, Y. Kishi, J. Org. Chem. 1987, 52, 4819;
7. b) P. G. Goekjian, T.-C. Wu, H.-Y. Kang, Y. Kishi, ibid. 1987, 52, 4823;
8. c) S. A. Babirad, Y. Wang, P. G. Goekjian, Y. Kishi, ibid. 1987, 52, 4825;
9. d) A. Wei, K. M. Boy, Y. Kishi, J. Am. Chem. Soc. 1995, 117, 9432;
10. e) A. Wei, A. Haudrechy, C. Audin, H.-S. Jun, N. Haudrechy-Bretel, Y. Kishi, J. Org. Chem. 1995, 60, 2160 and previous work.
11. For other conformational studies: a) A. Neuman, F. Longchambon, O. Abbes, H. Gillier-Pandraud, S. Pérez, D. Rouzaud, P. Sinaÿ, Carbohydr. Res. 1990, 195, 187; b) O. R. Martin, W. Lai, J. Org. Chem. 1993, 58, 176; c) K. N. Houk, J. E. Eksterowicz, Y-D. Wu, C. D. Fuglesang, D. B. Mitchell, J. Am. Chem. Soc. 1993, 115, 4170; d) C. A. Duda, E. S. Stevens, ibid. 1993, 115, 8487; e) J.-F. Espinosa, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Tetrahedron. Lett. 1996, 37, 1467; f) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Angew. Chem. 1996, 108, 323; Angew. Chem. Int. Ed. Engl. 1996, 35, 303; g) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, M. Martin-Pastor, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, J. Am. Chem. Soc. 1996, 118, 10862.
12. For other conformational studies: a) A. Neuman, F. Longchambon, O. Abbes, H. Gillier-Pandraud, S. Pérez, D. Rouzaud, P. Sinaÿ, Carbohydr. Res. 1990, 195, 187; b) O. R. Martin, W. Lai, J. Org. Chem. 1993, 58, 176; c) K. N. Houk, J. E. Eksterowicz, Y-D. Wu, C. D. Fuglesang, D. B. Mitchell, J. Am. Chem. Soc. 1993, 115, 4170; d) C. A. Duda, E. S. Stevens, ibid. 1993, 115, 8487; e) J.-F. Espinosa, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Tetrahedron. Lett. 1996, 37, 1467; f) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Angew. Chem. 1996, 108, 323; Angew. Chem. Int. Ed. Engl. 1996, 35, 303; g) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, M. Martin-Pastor, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, J. Am. Chem. Soc. 1996, 118, 10862.
13. For other conformational studies: a) A. Neuman, F. Longchambon, O. Abbes, H. Gillier-Pandraud, S. Pérez, D. Rouzaud, P. Sinaÿ, Carbohydr. Res. 1990, 195, 187; b) O. R. Martin, W. Lai, J. Org. Chem. 1993, 58, 176; c) K. N. Houk, J. E. Eksterowicz, Y-D. Wu, C. D. Fuglesang, D. B. Mitchell, J. Am. Chem. Soc. 1993, 115, 4170; d) C. A. Duda, E. S. Stevens, ibid. 1993, 115, 8487; e) J.-F. Espinosa, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Tetrahedron. Lett. 1996, 37, 1467; f) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Angew. Chem. 1996, 108, 323; Angew. Chem. Int. Ed. Engl. 1996, 35, 303; g) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, M. Martin-Pastor, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, J. Am. Chem. Soc. 1996, 118, 10862.
14. For other conformational studies: a) A. Neuman, F. Longchambon, O. Abbes, H. Gillier-Pandraud, S. Pérez, D. Rouzaud, P. Sinaÿ, Carbohydr. Res. 1990, 195, 187; b) O. R. Martin, W. Lai, J. Org. Chem. 1993, 58, 176; c) K. N. Houk, J. E. Eksterowicz, Y-D. Wu, C. D. Fuglesang, D. B. Mitchell, J. Am. Chem. Soc. 1993, 115, 4170; d) C. A. Duda, E. S. Stevens, ibid. 1993, 115, 8487; e) J.-F. Espinosa, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Tetrahedron. Lett. 1996, 37, 1467; f) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Angew. Chem. 1996, 108, 323; Angew. Chem. Int. Ed. Engl. 1996, 35, 303; g) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, M. Martin-Pastor, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, J. Am. Chem. Soc. 1996, 118, 10862.
15. For other conformational studies: a) A. Neuman, F. Longchambon, O. Abbes, H. Gillier-Pandraud, S. Pérez, D. Rouzaud, P. Sinaÿ, Carbohydr. Res. 1990, 195, 187; b) O. R. Martin, W. Lai, J. Org. Chem. 1993, 58, 176; c) K. N. Houk, J. E. Eksterowicz, Y-D. Wu, C. D. Fuglesang, D. B. Mitchell, J. Am. Chem. Soc. 1993, 115, 4170; d) C. A. Duda, E. S. Stevens, ibid. 1993, 115, 8487; e) J.-F. Espinosa, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Tetrahedron. Lett. 1996, 37, 1467; f) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Angew. Chem. 1996, 108, 323; Angew. Chem. Int. Ed. Engl. 1996, 35, 303; g) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, M. Martin-Pastor, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, J. Am. Chem. Soc. 1996, 118, 10862.
16. For other conformational studies: a) A. Neuman, F. Longchambon, O. Abbes, H. Gillier-Pandraud, S. Pérez, D. Rouzaud, P. Sinaÿ, Carbohydr. Res. 1990, 195, 187; b) O. R. Martin, W. Lai, J. Org. Chem. 1993, 58, 176; c) K. N. Houk, J. E. Eksterowicz, Y-D. Wu, C. D. Fuglesang, D. B. Mitchell, J. Am. Chem. Soc. 1993, 115, 4170; d) C. A. Duda, E. S. Stevens, ibid. 1993, 115, 8487; e) J.-F. Espinosa, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Tetrahedron. Lett. 1996, 37, 1467; f) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Angew. Chem. 1996, 108, 323; Angew. Chem. Int. Ed. Engl. 1996, 35, 303; g) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, M. Martin-Pastor, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, J. Am. Chem. Soc. 1996, 118, 10862.
17. For other conformational studies: a) A. Neuman, F. Longchambon, O. Abbes, H. Gillier-Pandraud, S. Pérez, D. Rouzaud, P. Sinaÿ, Carbohydr. Res. 1990, 195, 187; b) O. R. Martin, W. Lai, J. Org. Chem. 1993, 58, 176; c) K. N. Houk, J. E. Eksterowicz, Y-D. Wu, C. D. Fuglesang, D. B. Mitchell, J. Am. Chem. Soc. 1993, 115, 4170; d) C. A. Duda, E. S. Stevens, ibid. 1993, 115, 8487; e) J.-F. Espinosa, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Tetrahedron. Lett. 1996, 37, 1467; f) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Angew. Chem. 1996, 108, 323; Angew. Chem. Int. Ed. Engl. 1996, 35, 303; g) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, M. Martin-Pastor, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, J. Am. Chem. Soc. 1996, 118, 10862.
18. For other conformational studies: a) A. Neuman, F. Longchambon, O. Abbes, H. Gillier-Pandraud, S. Pérez, D. Rouzaud, P. Sinaÿ, Carbohydr. Res. 1990, 195, 187; b) O. R. Martin, W. Lai, J. Org. Chem. 1993, 58, 176; c) K. N. Houk, J. E. Eksterowicz, Y-D. Wu, C. D. Fuglesang, D. B. Mitchell, J. Am. Chem. Soc. 1993, 115, 4170; d) C. A. Duda, E. S. Stevens, ibid. 1993, 115, 8487; e) J.-F. Espinosa, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Tetrahedron. Lett. 1996, 37, 1467; f) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Angew. Chem. 1996, 108, 323; Angew. Chem. Int. Ed. Engl. 1996, 35, 303; g) J.-F. Espinosa, F. J. Cañada, J. L. Asensio, M. Martin-Pastor, H. Dietrich, M. Martin-Lomas, R. R. Schmidt, J. Jiménez-Barbero, J. Am. Chem. Soc. 1996, 118, 10862.
19. a) M. D. Sinnott, P. J. Smith, J. Chem. Soc. Chem. Commun. 1976, 223;
20. b) J.-C. Tang, B. E. Tropp, R. Engel, Tetrahedron Lett. 1978, 723;
21. c) D. W. Norbeck, J. B. Kramer, P. A. Lartey, J. Org. Chem. 1987, 52, 2174;
22. d) J. N. BeMiller, M. P. Yadar, V. N. Kalabokis, R. W. Myers, Carbohydr. Res. 1990, 200, 111;
23. e) R. R. Schmidt, H. Dietrich, Angew. Chem. 1991, 103, 1348; Angew. Chem. Int. Ed. Engl. 1991, 30, 1328.
24. e) R. R. Schmidt, H. Dietrich, Angew. Chem. 1991, 103, 1348; Angew. Chem. Int. Ed. Engl. 1991, 30, 1328.
25. a) W. Spevak, J. O. Nagy, D. H. Charych, M. E. Schaefer, J. H. Gilbert, M. D. Bednarski, J. Am. Chem. Soc. 1993, 115, 1146;
26. b) J. O. Nagy, P. Wang, J. H. Gilbert, M. E. Schaefer, T. G. Hill, M. R. Callstrom, M. D. Bednarski, J. Med. Chem. 1992, 35, 4501;
27. C. R. Bertozzi, D. G. Cook, W. R. Kobertz, F. Gonzalez-Scarano, M. D. Bednarski, J. Am. Chem. Soc. 1992, 114, 10639;
28. d) C. R. Bertozzi, M. D. Bednarski, ibid. 1992, 114, 5543;
29. e) C. R. Bertozzi, P. D. Hoeprich, M. D. Bednarski, J. Org. Chem. 1992, 57, 6092;
30. f) C. R. Bertozzi, M. D. Bednarski, Carbohydr. Res. 1992, 223, 243;
31. g) T. Uchiyama, T. J. Woltering, W. Wong, C.-C. Lin, T. Kajimoto, M. Takebayashi, G. Weitz-Schmidt, T. Asakura, M. Noda, C.-H. Wong, Bioorg. Med. Chem. 1996, 4, 1149;
32. h) R. V. Weatherman, L. L. Kiessling, J. Org. Chem. 1996, 61, 534.
33. [3f, g]
34. a) A. De Mesmaeker, P. Hoffmann, B. Ernst, P. Hug, T. Winkler, Tetrahedron Lett. 1989, 30, 6307;
35. b) A. De Mesmaeker, P. Hoffmann, B. Ernst, P. Hug, T. Winkler, ibid. 1989, 30, 6311;
36. c) A. De Mesmaeker, A. Waldner, P. Hoffmann, T. Mindt, P. Hug, T. Winkler, Synlett 1990, 687;
37. d) A. De Mesmaeker, A. Waldner, P. Hoffmann, P. Hug, T. Winkler, ibid. 1992, 285;
38. e) A. De Mesmaeker, A. Waldner, P. Hoffmann, T. Winkler, ibid. 1994, 330;
39. f) G. Stork, H. S. Suh, G. Kim, J. Am. Chem. Soc. 1991, 113, 7054.
40. 8-endo and 9-endo tethered radical cyclizations have also been exploited for the synthesis of C-disaccharides. a) Y. C. Yin, J.-M. Mallet, P. Sinaÿ, J. Chem. Soc. Chem. Commun. 1993, 864; b) B. Vauzeilles, J.-M. Mallet, P. Sinaÿ, Synlett 1993, 522; c) A. Mallet, J.-M. Mallet, P. Sinaÿ, Tetrahedron Asym. 1994, 5, 2593; d) A. Chénedé, E. Rekaï, E. Perrin, P. Sinaÿ, Synlett 1994, 414.
41. 8-endo and 9-endo tethered radical cyclizations have also been exploited for the synthesis of C-disaccharides. a) Y. C. Yin, J.-M. Mallet, P. Sinaÿ, J. Chem. Soc. Chem. Commun. 1993, 864; b) B. Vauzeilles, J.-M. Mallet, P. Sinaÿ, Synlett 1993, 522; c) A. Mallet, J.-M. Mallet, P. Sinaÿ, Tetrahedron Asym. 1994, 5, 2593; d) A. Chénedé, E. Rekaï, E. Perrin, P. Sinaÿ, Synlett 1994, 414.
42. 8-endo and 9-endo tethered radical cyclizations have also been exploited for the synthesis of C-disaccharides. a) Y. C. Yin, J.-M. Mallet, P. Sinaÿ, J. Chem. Soc. Chem. Commun. 1993, 864; b) B. Vauzeilles, J.-M. Mallet, P. Sinaÿ, Synlett 1993, 522; c) A. Mallet, J.-M. Mallet, P. Sinaÿ, Tetrahedron Asym. 1994, 5, 2593; d) A. Chénedé, E. Rekaï, E. Perrin, P. Sinaÿ, Synlett 1994, 414.
43. 8-endo and 9-endo tethered radical cyclizations have also been exploited for the synthesis of C-disaccharides. a) Y. C. Yin, J.-M. Mallet, P. Sinaÿ, J. Chem. Soc. Chem. Commun. 1993, 864; b) B. Vauzeilles, J.-M. Mallet, P. Sinaÿ, Synlett 1993, 522; c) A. Mallet, J.-M. Mallet, P. Sinaÿ, Tetrahedron Asym. 1994, 5, 2593; d) A. Chénedé, E. Rekaï, E. Perrin, P. Sinaÿ, Synlett 1994, 414.
44. 2 in organic synthesis, see: a) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307; b) G. A. Molander, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, S. Schreiber), Pergamon, Oxford (UK), 1991, Vol. 1, p. 251; c) G. A. Molander, in Organic Reactions (Ed.: L. A. Paquette), Wiley, New York, 1994, Vol. 46, p. 211; G. A. Molander, Chem. Rev. 1992, 92, 29; e) D. P. Curran, T. L. Fevig, C. P. Jaspersen, M. L. Totleben, Synlett 1992, 943; f) H. B. Kagan, J. L. Namy, Tetrahedron 1986, 42, 6573.
45. 2 in organic synthesis, see: a) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307; b) G. A. Molander, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, S. Schreiber), Pergamon, Oxford (UK), 1991, Vol. 1, p. 251; c) G. A. Molander, in Organic Reactions (Ed.: L. A. Paquette), Wiley, New York, 1994, Vol. 46, p. 211; G. A. Molander, Chem. Rev. 1992, 92, 29; e) D. P. Curran, T. L. Fevig, C. P. Jaspersen, M. L. Totleben, Synlett 1992, 943; f) H. B. Kagan, J. L. Namy, Tetrahedron 1986, 42, 6573.
46. 2 in organic synthesis, see: a) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307; b) G. A. Molander, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, S. Schreiber), Pergamon, Oxford (UK), 1991, Vol. 1, p. 251; c) G. A. Molander, in Organic Reactions (Ed.: L. A. Paquette), Wiley, New York, 1994, Vol. 46, p. 211; G. A. Molander, Chem. Rev. 1992, 92, 29; e) D. P. Curran, T. L. Fevig, C. P. Jaspersen, M. L. Totleben, Synlett 1992, 943; f) H. B. Kagan, J. L. Namy, Tetrahedron 1986, 42, 6573.
47. 2 in organic synthesis, see: a) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307; b) G. A. Molander, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, S. Schreiber), Pergamon, Oxford (UK), 1991, Vol. 1, p. 251; c) G. A. Molander, in Organic Reactions (Ed.: L. A. Paquette), Wiley, New York, 1994, Vol. 46, p. 211; d) G. A. Molander, Chem. Rev. 1992, 92, 29; e) D. P. Curran, T. L. Fevig, C. P. Jaspersen, M. L. Totleben, Synlett 1992, 943; f) H. B. Kagan, J. L. Namy, Tetrahedron 1986, 42, 6573.
48. 2 in organic synthesis, see: a) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307; b) G. A. Molander, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, S. Schreiber), Pergamon, Oxford (UK), 1991, Vol. 1, p. 251; c) G. A. Molander, in Organic Reactions (Ed.: L. A. Paquette), Wiley, New York, 1994, Vol. 46, p. 211; G. A. Molander, Chem. Rev. 1992, 92, 29; e) D. P. Curran, T. L. Fevig, C. P. Jaspersen, M. L. Totleben, Synlett 1992, 943; f) H. B. Kagan, J. L. Namy, Tetrahedron 1986, 42, 6573.
49. 2 in organic synthesis, see: a) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307; b) G. A. Molander, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, S. Schreiber), Pergamon, Oxford (UK), 1991, Vol. 1, p. 251; c) G. A. Molander, in Organic Reactions (Ed.: L. A. Paquette), Wiley, New York, 1994, Vol. 46, p. 211; G. A. Molander, Chem. Rev. 1992, 92, 29; e) D. P. Curran, T. L. Fevig, C. P. Jaspersen, M. L. Totleben, Synlett 1992, 943; f) H. B. Kagan, J. L. Namy, Tetrahedron 1986, 42, 6573.
50. a) D. Mazéas, T. Skrydstrup, O. Doumeix, J.-M. Beau, Angew. Chem. 1994, 106, 1457; Angew. Chem. Int. Ed. Engl. 1994, 33, 1383;
51. a) D. Mazéas, T. Skrydstrup, O. Doumeix, J.-M. Beau, Angew. Chem. 1994, 106, 1457; Angew. Chem. Int. Ed. Engl. 1994, 33, 1383;
52. b) D. Mazéas, T. Skrydstrup, M. Elmouchir, G. Doisneau, J.-M. Beau, Chem. Eur. J. 1997, 3, 1342.
53. Part of this work was previously published as a preliminary communication. a) D. Mazéas, T. Skrydstrup, J.-M. Beau, Angew. Chem. 1995, 107, 990; Angew. Chem. Int. Ed. Engl. 1995, 34, 909; b) O. Jarreton, T. Skrydstrup, J.-M. Beau, Tetrahedron Lett. 1997, 36, 303.
54. Part of this work was previously published as a preliminary communication. a) D. Mazéas, T. Skrydstrup, J.-M. Beau, Angew. Chem. 1995, 107, 990; Angew. Chem. Int. Ed. Engl. 1995, 34, 909; b) O. Jarreton, T. Skrydstrup, J.-M. Beau, Tetrahedron Lett. 1997, 36, 303.
55. Part of this work was previously published as a preliminary communication. a) D. Mazéas, T. Skrydstrup, J.-M. Beau, Angew. Chem. 1995, 107, 990; Angew. Chem. Int. Ed. Engl. 1995, 34, 909; b) O. Jarreton, T. Skrydstrup, J.-M. Beau, Tetrahedron Lett. 1997, 36, 303.
56. a) J.-M. Lancelin, L. Morin-Allory, P. Sinaÿ, J. Chem. Soc. Chem. Commun. 1984, 355;
57. b) J. Prandi, J.-M. Beau, Tetrahedron Lett. 1989, 30, 4517;
58. c) V. Wittman, H. Kessler, Angew. Chem. 1993, 105, 1138; Angew. Chem. Int. Ed. Engl. 1993, 32, 1091;
59. c) V. Wittman, H. Kessler, Angew. Chem. 1993, 105, 1138; Angew. Chem. Int. Ed. Engl. 1993, 32, 1091;
60. d) P. Lesimple, J.-M. Beau, Bioorg. Med. Chem. 1994, 2, 1319;
61. e) M. Hoffmann, H. Kessler, Tetrahedron Lett. 1994, 35, 6067;
62. f) O. Frey, M. Hoffmann, H. Kessler, Angew. Chem. 1995, 107, 2194; Angew. Chem. Int. Ed. Engl. 1995, 34, 2026.
63. f) O. Frey, M. Hoffmann, H. Kessler, Angew. Chem. 1995, 107, 2194; Angew. Chem. Int. Ed. Engl. 1995, 34, 2026.
64. a) T. Cohen, M.-T. Lin, J. Am. Chem. Soc. 1984, 106, 1130;
65. b) E. J. Verner, T. Cohen, ibid. 1992, 114, 375;
66. c) T. Cohen, M. Bhupathy, Acc. Chem. Res. 1989, 22, 152;
67. d) V. Pedretti, A. Veyrières, P. Sinaÿ, Tetrahedron 1990, 46, 77;
68. e) M. S. Ermolenko, A. Olesker, G. Lukas, Tetrahedron Lett. 1994, 35, 715; for related systems, see also:
69. f) S. D. Rychnovsky, D. E. Mickus, ibid. 1989, 30, 3011;
70. g) S. D. Rychnovsky, J. Org. Chem. 1989, 54, 4982.
71. a) J.-M. Beau, P. Sinaÿ, Tetrahedron Lett. 1985, 26, 6185;
72. b) J.-M. Beau, P. Sinaÿ, ibid. 1985, 26, 6189;
73. c) J.-M. Beau, P. Sinaÿ, ibid. 1985, 26, 6193;
74. d) D. Crich, L. M. L. Lim, ibid. 1990, 31, 1897.
75. a) P. Lesimple, J.-M. Beau, P. Sinaÿ, J. Chem. Soc. Chem. Commun. 1985, 894;
76. b) P. Lesimple, J.-M. Beau, P. Sinaÿ, Carbohydr. Res. 1987, 171, 289;
77. D. K. Hutchinson, P. L. Fuchs, J. Am. Chem. Soc. 1987, 109, 4930;
78. d) J. Prandi, C. Audin, J.-M. Beau, Tetrahedron Lett. 1991, 32, 769;
79. e) O. Frey, M. Hoffmann, V. Wittmann, H. Kessler, P. Uhlmann, A. Vasella, Helv. Chim. Acta 1994, 77, 2060;
80. f) M. Hoffmann, F. Burkhart, G. Hessler, H. Kessler, ibid. 1996, 79, 1519.
81. a) J. B. Ousset, C. Mioskowski, Y.-L. Yang, J. R. Falk, Tetrahedron Lett. 1984, 25, 5903;
82. b) S. Ley, B. Lygo, ibid. 1984, 25, 113;
83. c) R. R. Schmidt, J. Kast, ibid. 1986, 27, 4007;
84. d) I. Dancy, T. Skrydstrup, C. Crévisy, J.-M. Beau, J. Chem. Soc. Chem. Commun. 1995, 799;
85. e) B. Aebisher, J. H. Bieri, P. Prewo, A. Vasella, Helv. Chim. Acta 1982, 65, 2251;
86. f) K. Mahmood, A. Vasella, B. Bernet, ibid. 1991, 74, 1555, and references therein;
87. g) A. M. Griffin, N. J. Newcombe, D. Alker, M. V. J. Ramsay, T. Gallagher, Heterocycles 1993, 35, 1247;
88. h) N. J. Newcombe, M. F. Mahon, K. C. Malloy, D. Alker, T. Gallagher, J. Am. Chem. Soc. 1995, 115, 6430.
89. a) P. Lesimple, J.-M. Beau, G. Jaurand, P. Sinaÿ, Tetrahedron Lett. 1986, 27, 6201;
90. b) K. C. Nicolaou, C.-K. Hwang, M. E. Duggan, J. Chem. Soc. Chem. Commun. 1986, 925;
91. c) S. Hanessian, M. Martin, R. C. Desai, ibid. 1986, 926;
92. d) K. A. Parker, C. A. Coburn, J. Am. Chem. Soc. 1991, 113, 8516;
93. e) K. A. Parker, C. A. Coburn, J. Org. Chem. 1992, 57, 5547;
94. f) K. A. Parker, D.-S. Su, ibid. 1996, 61, 2191;
95. g) K. A. Parker, Y.-H. Koh, J. Am. Chem. Soc. 1994, 116, 11149;
96. h) M. A. Tius, X. Gu, J. Gomez-Galeno, ibid. 1990, 112, 8188;
97. M. A. Tius, X. Gu, J. H. Zaidi, ibid. 1991, 113, 5775;
98. j) R. R. Schmidt, R. Preuss, R. Betz, Tetrahedron Lett. 1987, 28, 6591;
99. k) R. Preuss, R. R. Schmidt, Liebigs Ann. Chem. 1989, 429;
100. l) R. R. Schmidt, H. Dietrich, Angew. Chem. 1991, 103, 1348; Angew. Chem. Int. Ed. Engl. 1991, 30, 1328;
101. l) R. R. Schmidt, H. Dietrich, Angew. Chem. 1991, 103, 1348; Angew. Chem. Int. Ed. Engl. 1991, 30, 1328;
102. m) R. R. Schmidt, R. Preuss, Tetrahedron Lett. 1989, 30, 3409;
103. n) S. Maier, R. Preuss, R. R. Schmidt, Liebigs Ann. Chem. 1990, 483;
104. o) R. W. Friesen, C. F. Sturino, A. K. Daljeet, A. E. Kolaczewska, J. Org. Chem. 1991, 56, 1994;
105. p) R. W. Friesen, L. A. Trimble, ibid. 1996, 61, 1165;
106. q) For a recent review on nucleophilic C-glycosyl donors, J.-M. Beau, T. Gallagher, in Top. Curr. Chem. Vol. 187(Eds.: H. Driguez, J. Thiem), Springer, Berlin, 1997, p. 1.
107. [16e, f] In addition, anomeric manganese, cobalt, and iron complexes have been found to be stable towards β elimination: a) P. DeShong, G. A. Slough, V. Elango, G. L. Trainor, J. Am. Chem. Soc. 1985, 107, 7788; b) P. DeShong, G. A. Slough, V. Elango, Carbohydr. Res. 1987, 171, 342; c) P. DeShong, G. A. Slough, A. L. Rheingold, Tetrahedron Lett. 1987, 28, 2229; d) P. DeShong, D. R. Sidler, A. L. Rheingold, ibid. 1987, 28, 2233; e) H. Chatani, T. Ikeda, T. Sano, N. Sonoda, H. Kurosawa, Y. Kawasaki, S. Murai, J. Org. Chem. 1988, 53, 3387; f) G. L. Trainer, B. E. Smart, ibid. 1983, 48, 2447.
108. [16e, f] In addition, anomeric manganese, cobalt, and iron complexes have been found to be stable towards β elimination: a) P. DeShong, G. A. Slough, V. Elango, G. L. Trainor, J. Am. Chem. Soc. 1985, 107, 7788; b) P. DeShong, G. A. Slough, V. Elango, Carbohydr. Res. 1987, 171, 342; c) P. DeShong, G. A. Slough, A. L. Rheingold, Tetrahedron Lett. 1987, 28, 2229; d) P. DeShong, D. R. Sidler, A. L. Rheingold, ibid. 1987, 28, 2233; e) H. Chatani, T. Ikeda, T. Sano, N. Sonoda, H. Kurosawa, Y. Kawasaki, S. Murai, J. Org. Chem. 1988, 53, 3387; f) G. L. Trainer, B. E. Smart, ibid. 1983, 48, 2447.
109. [16e, f] In addition, anomeric manganese, cobalt, and iron complexes have been found to be stable towards β elimination: a) P. DeShong, G. A. Slough, V. Elango, G. L. Trainor, J. Am. Chem. Soc. 1985, 107, 7788; b) P. DeShong, G. A. Slough, V. Elango, Carbohydr. Res. 1987, 171, 342; c) P. DeShong, G. A. Slough, A. L. Rheingold, Tetrahedron Lett. 1987, 28, 2229; d) P. DeShong, D. R. Sidler, A. L. Rheingold, ibid. 1987, 28, 2233; e) H. Chatani, T. Ikeda, T. Sano, N. Sonoda, H. Kurosawa, Y. Kawasaki, S. Murai, J. Org. Chem. 1988, 53, 3387; f) G. L. Trainer, B. E. Smart, ibid. 1983, 48, 2447.
110. [16e, f] In addition, anomeric manganese, cobalt, and iron complexes have been found to be stable towards β elimination: a) P. DeShong, G. A. Slough, V. Elango, G. L. Trainor, J. Am. Chem. Soc. 1985, 107, 7788; b) P. DeShong, G. A. Slough, V. Elango, Carbohydr. Res. 1987, 171, 342; c) P. DeShong, G. A. Slough, A. L. Rheingold, Tetrahedron Lett. 1987, 28, 2229; d) P. DeShong, D. R. Sidler, A. L. Rheingold, ibid. 1987, 28, 2233; e) H. Chatani, T. Ikeda, T. Sano, N. Sonoda, H. Kurosawa, Y. Kawasaki, S. Murai, J. Org. Chem. 1988, 53, 3387; f) G. L. Trainer, B. E. Smart, ibid. 1983, 48, 2447.
111. [16e, f] In addition, anomeric manganese, cobalt, and iron complexes have been found to be stable towards β elimination: a) P. DeShong, G. A. Slough, V. Elango, G. L. Trainor, J. Am. Chem. Soc. 1985, 107, 7788; b) P. DeShong, G. A. Slough, V. Elango, Carbohydr. Res. 1987, 171, 342; c) P. DeShong, G. A. Slough, A. L. Rheingold, Tetrahedron Lett. 1987, 28, 2229; d) P. DeShong, D. R. Sidler, A. L. Rheingold, ibid. 1987, 28, 2233; e) H. Chatani, T. Ikeda, T. Sano, N. Sonoda, H. Kurosawa, Y. Kawasaki, S. Murai, J. Org. Chem. 1988, 53, 3387; f) G. L. Trainer, B. E. Smart, ibid. 1983, 48, 2447.
112. [16e, f] In addition, anomeric manganese, cobalt, and iron complexes have been found to be stable towards β elimination: a) P. DeShong, G. A. Slough, V. Elango, G. L. Trainor, J. Am. Chem. Soc. 1985, 107, 7788; b) P. DeShong, G. A. Slough, V. Elango, Carbohydr. Res. 1987, 171, 342; c) P. DeShong, G. A. Slough, A. L. Rheingold, Tetrahedron Lett. 1987, 28, 2229; d) P. DeShong, D. R. Sidler, A. L. Rheingold, ibid. 1987, 28, 2233; e) H. Chatani, T. Ikeda, T. Sano, N. Sonoda, H. Kurosawa, Y. Kawasaki, S. Murai, J. Org. Chem. 1988, 53, 3387; f) G. L. Trainer, B. E. Smart, ibid. 1983, 48, 2447.
113. Recently, generation of anomeric titanium(IV) complexes have been shown to be a viable route for the preparation of glycals due to their rapid β elimination. a) C. L. Cavallaro, J. Schwartz, J. Org. Chem. 1996, 61, 534; b) R. P. Spencer, J. Schwartz, Tetrahedron Lett. 1996, 37, 4357.
114. Recently, generation of anomeric titanium(IV) complexes have been shown to be a viable route for the preparation of glycals due to their rapid β elimination. a) C. L. Cavallaro, J. Schwartz, J. Org. Chem. 1996, 61, 534; b) R. P. Spencer, J. Schwartz, Tetrahedron Lett. 1996, 37, 4357.
115. a) H. Künzer, M. Stahnke, G. Sauer, R. Wiechert, Tetrahedron Lett. 1991, 32, 1949;
116. b) P. de Pouilly, A. Chénedé, J.-M. Mallet, P Sinaÿ, ibid. 1992, 33, 8065;
117. c) P. de Pouilly, A. Chénedé, J.-M. Mallet, P. Sinaÿ, Bull. Soc. Chim. Fr. 1993, 130, 256;
118. d) M. Ihara, S. Suzuki, T. Taniguchi, Y. Tokunaga, K. Fukumoto, Synlett 1994, 859;
119. e) J. Clayden, M. Julia, J. Chem. Soc. Chem. Commun. 1994, 2261;
120. f) G. A. Keck, K. A. Savin, M. A. Weglarz, J. Org. Chem. 1995, 60, 3194.
121. For exceptions, see a) A. Kende, J. S. Mendoga, Tetrahedron Lett. 1990, 31, 7105; b) B. M. Trost, J. B. Nielsen, K. Hoogsteen, J. Am. Chem. Soc. 1992, 114, 5432; c) S. Chandrasekhar, J. Yu, J. R. Falck, C. Mioskowski, Tetrahedron Lett. 1994, 35, 5441.
122. For exceptions, see a) A. Kende, J. S. Mendoga, Tetrahedron Lett. 1990, 31, 7105; b) B. M. Trost, J. B. Nielsen, K. Hoogsteen, J. Am. Chem. Soc. 1992, 114, 5432; c) S. Chandrasekhar, J. Yu, J. R. Falck, C. Mioskowski, Tetrahedron Lett. 1994, 35, 5441.
123. For exceptions, see a) A. Kende, J. S. Mendoga, Tetrahedron Lett. 1990, 31, 7105; b) B. M. Trost, J. B. Nielsen, K. Hoogsteen, J. Am. Chem. Soc. 1992, 114, 5432; c) S. Chandrasekhar, J. Yu, J. R. Falck, C. Mioskowski, Tetrahedron Lett. 1994, 35, 5441.
124. 2/HMPA combination.
125. S. D. Rychnovsky, J. P. Powers, T. L. LePage, J. Am. Chem. Soc. 1992, 114, 8375.
126. For a mechanistic discussion of the Barbier reaction with samarium compounds, see a) G. A. Molander, J. A. McKie, J. Org. Chem. 1991, 56, 4112; b) J. L. Namy, J. Collin, C. Bied, H. B. Kagan, Synlett 1992, 733, and ref. [9b].
127. For a mechanistic discussion of the Barbier reaction with samarium compounds, see a) G. A. Molander, J. A. McKie, J. Org. Chem. 1991, 56, 4112; b) J. L. Namy, J. Collin, C. Bied, H. B. Kagan, Synlett 1992, 733, and ref. [9b].
128. [26] led to a considerably greater amount of N-glycosylation products compared with that reported.
129. H. B. Mereyala, G. V. Reddy, Tetrahedron 1989, 47, 6435.
130. a) S. D. Rychnovsky, B. Rogers, G. Yang, J. Org. Chem. 1993, 58, 3511;
131. b) T. I. Richardson, S. D. Rychnovsky, ibid. 1996, 61, 4219.
132. S. Koto, N. Morishima, Y. Miyato, S. Zen. Bull. Chem. Soc. Japan 1976, 49, 2639.
133. a) J. Dupuis, B. Giese, D. Rüegge, H. Fischer, H.-G. Korth, R. Sustmann, Angew. Chem. 1984, 96, 887; Angew. Chem. Int. Ed. Engl. 1984, 23, 896;
134. a) J. Dupuis, B. Giese, D. Rüegge, H. Fischer, H.-G. Korth, R. Sustmann, Angew. Chem. 1984, 96, 887; Angew. Chem. Int. Ed. Engl. 1984, 23, 896;
135. b) H.-G. Korth, R. Sustmann, J. Dupuis, B. Giese, J. Chem. Soc. Perkin Trans. II 1986, 1453;
136. c) H. Chandra, M. C. R. Symons, Tetrahedron Lett. 1987, 28, 1455;
137. d) H.-G. Korth, R. Sustmann, J. Chem. Soc. Faraday Trans. I 1987, 95;
138. e) H.-G. Korth, R. Sustmann, B. Giese, B. Rückert, K. S. Gröninger, Chem. Ber. 1990, 123, 1891;
139. f) B. Giese, J. Dupuis, K. Kröniger, T. Hasskerl, M. Nix, T. Witzel, in Substituent Effects in Radical Chemistry (Eds.: H. G. Viehe, Z. Janousek, R. Merenyi), Reidel, Dordrecht, 1986, p. 285;
140. g) B. Giese, Angew. Chem. 1989, 101, 993; Angew. Chem. Int. Ed. Engl. 1989, 28, 969;
141. g) B. Giese, Angew. Chem. 1989, 101, 993; Angew. Chem. Int. Ed. Engl. 1989, 28, 969;
142. h) B. Giese, H.-G. Zetz, in Preparative Carbohydrate Chemistry (Ed.: S. Hanessian), M. Dekker, New York, 1997, p. 507.
143. Another possible explanation for the formation of β-C-glucosides and galactosides invokes the stereospecific reduction of the α-anomeric radical from the β-face, leading directly to the organosamarium 38, by the approach of the sterically bulky hepta-coordinated divalent samarium to the least hindered side of the radical. If this were the case, it would be difficult to explain the higher tendency of glucosyl and galactosyl organosamarium reagents to undergo β elimination compared with the analogous manno-series.
144. C2-O2 bonds such as in Table 2, entries 5 - 7, where trans-elimination is the probable mechanism.
145. P. von Ragué Schleyer, T. Clark, A. J. Kos, G. W. Spitznagel, C. Rohde, D. Arad, K. N. Houk, N. G. Rondan, J. Am. Chem. Soc. 1984, 106, 6467.
146. a) E. Hasegawa, D. P. Curran, Tetrahedron Lett. 1993, 34, 1717;
147. b) M. Shabangi, R. A. Flowers, II, ibid. 1997, 38, 1137.
148. 2 in the presence of HMPA see: a) K. Otsubo, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 5763; b) J. Inanaga, M. Ishigawa, M. Yamaguchi, Chem. Lett. 1987, 1485; c) K. Otsubo, J. Inanaga, M. Yamaguchi, ibid. 1987, 1487; d) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun. 1989, 298.
149. 2 in the presence of HMPA see: a) K. Otsubo, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 5763; b) J. Inanaga, M. Ishigawa, M. Yamaguchi, Chem. Lett. 1987, 1485; c) K. Otsubo, J. Inanaga, M. Yamaguchi, ibid. 1987, 1487; d) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun. 1989, 298.
150. 2 in the presence of HMPA see: a) K. Otsubo, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 5763; b) J. Inanaga, M. Ishigawa, M. Yamaguchi, Chem. Lett. 1987, 1485; c) K. Otsubo, J. Inanaga, M. Yamaguchi, ibid. 1987, 1487; d) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun. 1989, 298.
151. 2 in the presence of HMPA see: a) K. Otsubo, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 5763; b) J. Inanaga, M. Ishigawa, M. Yamaguchi, Chem. Lett. 1987, 1485; c) K. Otsubo, J. Inanaga, M. Yamaguchi, ibid. 1987, 1487; d) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun. 1989, 298.
152. 2 complex has recently been disclosed: Z. Hou, Y. Wakatsuki, J. Chem. Soc. Chem. Commun. 1994, 1205.
153. 2 complex has recently been disclosed: Z. Hou, Y. Wakatsuki, J. Chem. Soc. Chem. Commun. 1994, 1205.
154. O. Jarreton, T. Skrydstrup, J.-M. Beau, unpublished results.
155. 2, it is necessary to include an α-heteroatom as the endocyclic C5-oxygen which promotes easy fragmentation of the radical anion intermediate through stabilization of the anomeric radical. For other examples, see ref. [21] and T. Skrydstrup, T. M. Jespersen, J.-M. Beau, M. Bols, Chem. Commun. 1996, 515.
156. 3, iv) MCPBA. This synthesis will be reported elsewhere.
157. This C-glycosylation approach has been successfully applied to 2-deoxy-2-acetamido sugars, see D. Urban, T. Skrydstrup, C. Riche, A. Chiaroni, J.-M. Beau, Chem. Commun. 1996, 1883.
158. I. R. Vlahov, P. I. Vlahova, R. J. Linhardt, J. Am. Chem. Soc. 1997, 119, 1480.
159. a) H. E. Zimmerman, L. W. Linder, J. Org. Chem. 1985, 50, 1637;
160. b) H. O. House, B. A. Tefertiller, H. D. Olmstead, ibid. 1968, 33, 935;
161. H. O. House, B. M. Trost, ibid. 1965, 30, 2502.
162. a) J. Collin, J.-L. Namy, C. Bied, H. B. Kagan, Inorg. Chim. Acta 1987, 140, 29;
163. b) J.-L. Namy, J. Collin, J. Zhang, H. B. Kagan, J. Organomet. Chem. 1987, 328, 81;
164. c) J. Collin, J.-L. Namy, F. Dallemer, H. B. Kagan, J. Org. Chem. 1991, 56, 3118;
165. d) C. Bied, J. Collin, H. B. Kagan, Tetrahedron 1992, 48, 3877.
166. M. E. Jung, S. W. T. Choe, Tetrahedron Lett. 1993, 34, 6247.
167. We have recently applied this approach to the synthesis of a C-disaccharide analogue of methyl α-D-mannopyranosyl(α1 →2)-D-mannopyranoside. O. Jarreton, T. Skrydstrup, J.-M. Beau, Chem. Commun. 1996, 1661.
168. Since our report on the use of pyridyl sulfones for C-glycoside synthesis, Wong's group has successfully demonstrated the applicability of glycosyl phosphates as viable starting materials for the formation of glycosyl samarium(III) reagents. S.-C. Hung, C.-H. Wong, Angew. Chem. 1996, 108, 2700; Angew. Chem. Int. Ed. Engl. 1996, 35, 2671.
169. Since our report on the use of pyridyl sulfones for C-glycoside synthesis, Wong's group has successfully demonstrated the applicability of glycosyl phosphates as viable starting materials for the formation of glycosyl samarium(III) reagents. S.-C. Hung, C.-H. Wong, Angew. Chem. 1996, 108, 2700; Angew. Chem. Int. Ed. Engl. 1996, 35, 2671.
170. P. Girard, J.-L. Namy, H. B. Kagan, J. Am. Chem. Soc. 1980, 102, 2693.
171. F.-Y. Dupradeau, S.-I. Hakomori, T. Tatsushi, J. Chem. Soc. Chem. Commun. 1995, 221.