Diastereoselective addition of metal-coordinated and 'naked' tri-sec-butylborohydrides to a norephedrine-derived 2-acetyloxazolidine

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 14, 1992, Pages 1027-1029

  Manzoni, Leonardo ^a   Pilati, Tullio ^b   Poli, Giovanni ^a   Scolastico, Carlo ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b Centro per lo Studio delle Relazioni tra Struttura e Reattivita' Chimica ^*  (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 4544302195     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39920001027     Document Type: Article

References (34)

1. L. A. Paquette, T. L. Underiner and G. C. Gallucci, J. Org. Chem., 1992, 57, 86.
2. D. C. Wigfield, Tetrahedron, 1979, 35, 449.
3. R. R. Fraser and M. Stanciulescu, J. Am. Chem. Soc., 1987, 109, 1580.
4. E. P. Lodge and C. H. Heathcock, J. Am. Chem. Soc., 1987, 109, 3353.
5. A. S. Cieplak, B. D. Tait and B. R. Johnson, J. Am. Chem. Soc., 1989, 111, 8447.
6. Y. Kurita and C. Takayama, Tetrahedron, 1990, 46, 6633.
7. D. Mukherjee, Y-D. Wu, F. R. Fronkzek and K. N. Houk, J. Am. Chem. Soc., 1988, 110, 3328.
8. K. N. Houk and Y-D. Wu, Stereochemistry of Organic and Bioorganic Transformations, ed. W. Bartmann and K. B. Sharpless, VCH, New York, 1987; pp. 247-260.
9. S. S. Wong and M. N. Paddon-Row, J. Chem. Soc., Chem. Commun., 1990, 456.
10. S. S. Wong and M. N. Paddon-Row, J. Chem. Soc., Chem. Commun., 1991, 327.
11. Y.-D. Wu, J. A. Tucker and K. N. Houk, J. Am. Chem. Soc., 1991, 113, 5018.
12. A. S. Cieplak, J. Am. Chem. Soc., 1981, 103, 4540.
13. A. Bernardi, S. Cardani, T. Pilati, G. Poli, C. Scolastico and R. Villa, J. Org. Chem., 1988, 53, 1600.
14. S. Cardani, G. Poli, C. Scolastico and R. Villa, Tetrahedron, 1988, 44, 5929.
15. N. Greeves, in Comprehensive Organic Chemistry, ed. B. M. Trost, Pergamon Press, 1991, vol. 8, ch. 1. 1.
16. L. Colombo, C. Gennari, G. Poli, C. Scolastico and S. De Munari, Tetrahedron Lett., 1985, 26, 5459.
17. H. Redlich and B. Schneider, Liebigs Ann. Chem., 1983, 412.
18. A. Bernardi, G. Poli, C. Scolastico and M. Zanda, J. Org. Chem., 1990, 56, 6961.
19. D. P. Curran and J. Zhang, J. Chem. Soc., Perkin Trans. 1, 1991, 2613.
20. B. Dietrich, in Inclusion Compounds, ed. J. L. Atwood, J. E. D. Davies and D. D. McNicol, Academic Press, 1984, ch. 10, pp. 392-393.
21. J. L. Pierre and H. Handel, Tetrahedron Lett., 1974, 15, 2317.
22. A. Loupy, J. Seyden-Penne and B. Tchoubar, Tetrahedron Lett., 1976, 17, 1677.
23. K-J. Ko, W. J. Frazee and E. L. Eliel, Tetrahedron, 1984, 40, 1333.
24. S. V. Frye and E. L. Eliel, J. Am. Chem. Soc., 1987, 110, 484.
25. X. Chen, E. R. Hortelano, E. L. Eliel and S. V. Frye, J. Am. Chem. Soc., 1992, 114, 1778.
26. M. T. Reetz, Angew. Chem., Int. Ed. Engl., 1984, 23, 556.
27. S. Shambayati, S. L. Schreiber, in Comprehensive Organic Chemistry, ed. B. M. Trost, Pergamon, 1991, vol. 1, ch. 10.
28. W. Oppolzer, I. Rodriguez, J. Blagg and G. Bernardinelli, Helv. Chim. Acta, 1989, 72, 123.
29. W. Oppolzer, G. Poli, A. J. Kingma, C. Starkemann and G. Bernardinelli, Helv. Chim. Acta, 1987, 70, 2201.
30. K. N. Houk, M. N. Paddon-Row, N. G. Rondan, Y-D. Wu, F. K. Brown, D. C. Spellmeyer, J. T. Metz, Y. Li and R. J. Loncharich, Science, 1986, 231, 1108.
31. S. G. Pyne, P. Bloem and R. Griffith, Tetrahedron, 1989, 45, 7013.
32. G. Delogu, O. De Lucchi, P. Maglioli, Synlett, 1989, 28.
33. A. Bernardi, L. Colombo, C. Gennari and L. Prati, Tetrahedron, 1984, 40, 3775.
34. C. A. Hasnoot, F. A. DeLeeuw and C. Altona, Tetrahedron, 1980, 36, 2783.