Glycosylidene carbenes. Part 29. Insertion into B-C and Al-C bonds: Glycosylborinates, -boranes, and -alanes

Helvetica Chimica Acta

Volumn 83, Issue 7, 2000, Pages 1542-1560

  Wenger, Wolfgang ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; NUCLEAR OVERHAUSER EFFECT; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033930997     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20000705)83:7<1542::AID-HLCA1542>3.0.CO;2-F     Document Type: Article

References (51)

1. A. Vasella, W. Wenger, T. Rajamannar, Chem. Commun. 1999, 2215.
2. A. Vasella, in 'Biorganic Chemistry, Carbohydrates', Ed. S. Hecht, OUP, New York, 1999, 3.
3. M. Weber, A. Vasella, M. Textor, N. D. Spencer, Helv. Chim. Acta 1998, 81, 1359.
4. M. Weber, A. Vasella, Helv. Chim. Acta 1997, 80, 2352.
5. K. Briner, A. Vasella, Helv. Chim. Acta 1990, 73, 1764.
6. T. Rajamannar, A. Vasella, unpublished results.
7. A. Vasella, G. Baudin, L. Panza, J. Heteroatom Chem. 1991, 2, 151.
8. P. Uhlmann, D. Nanz, E. Bozo, A. Vasella, Helv. Chim. Acta 1994, 77, 1430.
9. M. H. D. Postema, Tetrahedron 1992, 48, 8545.
10. J.-M. Beau, T. Gallagher, in 'Topics in Current Chemistry', Eds. H. Driguez and J. Thiem, Springer Verlag, Berlin, 1997, 187, p. 1.
11. Y. Du, R. J. Linhardt, I. R. Vlahov, Tetrahedron 1998, 54, 9913.
12. D. S. Matteson, 'Stereodirected Synthesis with Organoboranes', Springer-Verlag, Heidelberg, 1995.
13. A. Pelter, K. Smith, in 'Comprehensive Organic Chemistry', Eds. D. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, 3, p. 821.
14. H. Hoberg, Justus Liebigs Ann. Chem. 1966, 695, 1.
15. E. Negishi, K. Akiyoshi, J. Am. Chem. Soc. 1988, 110, 646.
16. A. Pelter, K. Smith, H. C. Brown, 'Borane Reagents', Academic Press, London, 1988.
17. M. Vaulthier, B. Carboni, in 'Comprehensive Organometallic Chemistry II', Ed. A. McKillop, Pergamon, Oxford, 1994, 11, p. 191.
18. G. Hesse, A. Haag, Tetrahedron Lett. 1965, 1123.
19. D. Seyferth, B. Prokai, J. Am. Chem. Soc. 1966, 88, 1834.
20. G. Alcarez, R. Reed, A. Baceiredo, G. Bertrand, J. Chem. Soc., Chem. Commun. 1993, 1354.
21. A. Suzuki, S. Nozawa, N. Miyaura, M. Itoh, Tetrahedron Lett. 1969, 2955.
22. K. Briner, A. Vasella, Helv. Chim. Acta 1989, 72, 1371.
23. A. Vasella, C. Witzig, C. Waldraff, P. Uhlmann, K. Briner, B. Bernet, L. Panza, R. Husi, Helv. Chim. Acta 1993, 76, 2847.
24. J. A. Soderquist, M. R. Najafi, J. Org. Chem. 1986, 51, 1330.
25. J. A. Soderquist, J. Ramos, K. Matos, Tetrahedron Lett. 1997, 38, 6639.
26. B. Wrackmeyer, Prog. Nucl. Magn. Reson. Spectrosc. 1979, 12, 227.
27. H. Nöth, B. Wrackmeyer, NMR: Basic Principles and Progress 1978, 14, 138.
28. G. Giese, J. Dupuis, M. Leising, M. Nix, H. J. Lindner, Carbohydr. Res. 1987, 171, 329.
29. L. Parkanyi, A. Kalman, L. Somsak, J. Farkas, Carbohydr. Res. 1987, 168, 1.
30. L. Somsak, G. Batta, I. Farkas, L. Parkanyi, A. Kalman, A. Somogyi, J. Chem. Res., Synop. 1986, 436.
31. S. B. Rosenblum, R. Bihovsky, J. Am. Chem. Soc. 1990, 112, 2746.
32. S. Czernecki, G. Ville, J. Org. Chem. 1989, 54, 610.
33. A. M. Gomez, M. Casillas, S. Valverde, J. C. Lopez, Chem. Commun. 1996, 2357.
34. D. J. Pasto, R. Snyder, J. Org. Chem. 1966, 31, 2777.
35. D. J. Pasto, J. Hickman, J. Am. Chem. Soc. 1968, 90, 4445.
36. D. J. Pasto, C. C. Cumbo, J. Am. Chem. Soc. 1964, 86, 4343.
37. D. S. Matteson, J. Organomet. Chem. 1999, 581, 51.
38. H. C. Brown, E. F. Knights, J. Am. Chem. Soc. 1968, 90, 4439.
39. H. C. Brown, J. V. N. Vara Prasad, J. Org. Chem. 1985, 50, 3002.
40. Semichem, 'Ampac 5.0',7128 Summit, Shawnee, KS 66216, 1994.
41. G. A. Tolstikov, N. A. Prokhorova, A. Y. Spirak, L. M. Khalilov, V. R. Sultanmuratova, J. Org. Chem. USSR (Engl. Transl.) 1991, 27, 1858.
42. A. P. Kozikowski, T. Konoike, A. Ritter, Carbohydr. Res. 1987, 171, 109.
43. S. Hanessian, M. Martin, R. C. Desai, J. Chem. Soc. Chem. Commun. 1986, 926.
44. M. Witanowski, J. D. Roberts, J. Am. Chem. Soc. 1966, 88, 737.
45. J. J. Eisch, in 'Comprehensive Organometallic Chemistry I', Eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1982, 1, p. 555.
46. J. J. Eisch, K. C. Fichter, J. Am. Chem. Soc. 1974, 96, 6815.
47. P. Pino, G. P. Lorenzi, J. Org. Chem. 1966, 31, 329.
48. M. Sollogoub, J.-M. Mallet, P. Sinaÿ Angew. Chem. Int. Ed. 2000, 39, 362.
49. C. K. Johnson, 'ORTEPII, Report ORNL-5138', Oak Ridge National Laboratory, Tennessee, USA, 1976.
50. A. Altomare, B. Carrozzini, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. Moliterni, R. A. Rizzi, 'SIR97: A Package for Crystal Structure Solution by Direct Methods and Refinement', Istituto die Ricerea per lo Sviluppo di Metodologie Cristallografiche, CNR, Bari, Italy, 1997.
51. G. M. Sheldrick, 'SHELXL97: Program for the Refinement of Crystal Structures', University of Göttingen, Germany, 1997.