Regio- and stereo-chemical outcomes in the nucleophilic ring cleavage reactions of mono-epoxides derived from cis-1,2-dihydrocatechols

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 12, 1997, Pages 1779-1791

  Banwell, Martin G ^a,d   Haddad, Najiba ^b   Hudlicky, Tomas ^c,e   Nugent, Thomas C ^c,e   Mackay, Maureen F ^b   Richards, Sharon L ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b LA TROBE UNIVERSITY   (Australia)

^c VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^d AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^e University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748590303     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700733g     Document Type: Article

References (41)

1. For reviews on the applications of cis-1,2-dihydrocatechols in synthesis see: (a) H. A. J. Carless, Tetrahedron: Asymmetry, 1992, 3, 795;
2. (b) D. A. Widdowson, D. W. Ribbons and S. D. Thomas, Janssen Chim. Acta, 1990, 3;
3. (c) S. M. Brown and T. Hudlicky, The Use of Arene cis-Diols in Synthesis, in Organic Synthesis: Theory and practice, ed T. Hudlicky, JAI Press, Greenwich, CT, 1993, vol. 2, p. 113;
4. (d) T. Hudlicky and J. W. Reed, Advances in Asymmetric Synthesis, ed. A. Hassner, JAI Press, Greenwich, CT 1995, vol. 1, p. 271;
5. (e) T. Hudlicky and A. J. Thorpe, Chem. Commun., 1996, 1993.
6. For some notable examples see (a) S. V. Ley and L. L. Yeung, Synlett., 1992, 291;
7. (b) T. Hudlicky, J. D. Price, F. Rulin and T. Tsunoda, J. Am. Chem. Soc., 1990, 112, 9439;
8. (c) T. Hudlicky, J. Rouden, H. Luna and S. Allen, J. Am. Chem. Soc., 1990, 116, 5099.
9. For our earlier papers in this area see (a) M. Mandel and T. Hudlicky, Synlett., 1993, 418;
10. (b) J. Rouden and T. Hudlicky, J. Chem. Soc., Perkin Trans. 1, 1993, 1095 and references therein;
11. (c) M. G. Banwell and J. R. Dupuche, Chem. Commun., 1996, 869 and references therein.
12. One of us has previously described the reaction of the title monoepoxides and the corresponding aziridines with certain carbon-centred nucleophiles: T. Hudlicky, X. Tian, K. Konisburger and J. Rouden, J. Org. Chem., 1994, 59, 4037:
13. for a discussion of the possible mechanism plus further applications and details see T. Hudlicky, X. Tian, K. Königsberger, R. Maurya, J. Rouden and B. Fan, J. Am. Chem. Soc., 1996, 118, 10 752.
14. (a) Synthesis of (±)-4: see ref. 2(6) as well as K. Ramesh, M. S. Wolfe, Y. Lee, D. Vander Velde and R. T. Borchardt, J. Org. Chem., 1992, 57, 5861 and references therein;
15. (b) Synthesis of 5: T. Hudlicky, H. Luna, H. F. Olivo, C. Anderson, T. C. Nugent and J. D. Price, J. Chem. Soc., Perkin Trans. 1, 1991, 2907;
16. (c) Note the corrigendum regarding the structure of azido alcohol 23: J. Chem. Soc., Perkin Trans. 1, 1993, 535.
17. D. R. Dalton, V. P. Datta and D. C. Jones, J. Am. Chem. Soc., 1968, 90, 5498.
18. A. A. Haines, Methods for the Oxidation of Organic Compounds, Academic Press, London, 1985, p. 86.
19. C. H. Behrens and K. B. Sharpless, J. Org. Chem., 1985, 50, 5696.
20. M. F. Mackay, M. G. Banwell, M. E. Reum and S. L. Richards, Acta Crystallogr., Sect. C, 1992, 48, 70.
21. M. B. Smith, Compendium of Organic Synthetic Methods, Wiley, New York, 1992, vol. 7, p. 164.
22. (a) M. B. Smith, Compendium of Organic Synthetic Methods, Wiley, New York, 1992, vol. 7, p. 163;
23. (b) S. Ram and L. D. Spicer, Tetrahedron Lett., 1987, 515.
24. We thank Dr Joseph S. Merola, of Virginia Polytechnic Institute & State University, for providing us with the crystallographic data for azido alcohol 24.
25. T. Hudlicky, T. Nugent and W. Griffith, J. Org. Chem., 1994, 59, 7944.
26. T. C. Nugent, PhD Dissertation, Virginia Polytechnic Institute & State University, August 1995.
27. (a) B. M. Trost and G. M. Molander, J. Am. Chem. Soc., 1981, 103, 5969;
28. (b) B. M. Trost, G.-H. Kuo and T. Benneche, J. Am. Chem. Soc., 1988, 110, 621;
29. (c) D. R. Tueting, A. E. Echavarren and J. K. Stille, Tetrahedron, 1989, 45, 979.
30. T. Tsuda, Y. Horii, Y. Nakagawa, T. Ishida and T. Saegusa, J. Org. Chem., 1989, 54, 977.
31. T. Ukai, H. Kawazura, Y. Ishii, J. J. Bonnet and T. A. Ibers, J. Organomet. Chem., 1974, 65, 253.
32. C. R. Johnson, P. A. Plé, L. Su, M. J. Heeg and J. P. Adams, Synlett., 1992, 388.
33. X. Deruyttere, L. Dumortier, J. Van der Eycken and M. Vanderwalle, Synlett., 1992, 51.
34. (a) T. Tsuda, Y. Horii, Y. Nakagawa, T. Ishida and T. Saegusa, J. Org. Chem., 1989, 54, 977;
35. (b) M. Suzuki, Y. Oda and R. Noyori, J. Am. Chem. Soc., 1979, 101, 1623.
36. C. Altona, H. J. Geise and C. Romers, Tetrahedron, 1968, 24, 13.
37. M. G. Banwell, Org. Prep. Proced. Int., 1989, 21, 255.
38. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.
39. G. M. Sheldrick, SHELX-86. In Crystallographic Computings, ed. G. M. Sheldrick, C. Krüger and R. Goddard, Oxford University Press, 1985, pp. 175-189.
40. G. M. Sheldrick, SHELX-76, Program for Crystal Structure Determination, University of Cambridge, Cambridge, UK, 1976.
41. C. K. Johnson, ORTEPII, Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, USA, 1976.