Iodocyclisation studies on unsaturated α-hydroxy esters

Tetrahedron Letters

Volumn 39, Issue 40, 1998, Pages 7415-7418

  Macritchie, Jacqueline A ^a   Peakman, Torren M ^b   Silcock, Alan ^b   Willis, Christine L ^b  

^a AgrEvo UK Ltd   (United Kingdom)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; ENANTIOMER; SYNTHESIS; THERMODYNAMICS;

EID: 0032192285     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01611-6     Document Type: Article

References (22)

1. 1. See for example: Marshall, J. A. and Jiang, H., Tetrahedron Lett., 1998, 39, 1493; Wigchert, S.C. M., Thuring, J. W. J. F., and Zwanenburg, B., Tetrahedron Lett., 1997,38, 2321; Zoretic, P. A., Fang, H., Ribeiro, A. A. and Dubay, G., J. Org. Chem., 1998, 63, 1156..
2. 1. See for example: Marshall, J. A. and Jiang, H., Tetrahedron Lett., 1998, 39, 1493; Wigchert, S.C. M., Thuring, J. W. J. F., and Zwanenburg, B., Tetrahedron Lett., 1997,38, 2321; Zoretic, P. A., Fang, H., Ribeiro, A. A. and Dubay, G., J. Org. Chem., 1998, 63, 1156..
3. 1. See for example: Marshall, J. A. and Jiang, H., Tetrahedron Lett., 1998, 39, 1493; Wigchert, S.C. M., Thuring, J. W. J. F., and Zwanenburg, B., Tetrahedron Lett., 1997,38, 2321; Zoretic, P. A., Fang, H., Ribeiro, A. A. and Dubay, G., J. Org. Chem., 1998, 63, 1156..
4. 2. Macritchie, J. A., Silcock, A and Willis, C. L., Tetrahedron: Asymmetry, 1997,8, 3895.
5. 3. See for example: Bedford, S. B., Fenton, G., Knight, D. W. and Shaw, D. E., J. Chem. Soc., Perkin Trans 1, 1996, 1505; Ting, P. C and Bartlett, P. A., J. Am. Chem. Soc., 1984, 106, 2668; Tamura, Y., Hojo, M., Kawamura, Sawada, S., and Yoshida, Z., J. Org. Chem., 1987, 53, 4062; Maier, M. E., Kandler, H., Haller, B. U., Hoffman, J. H., and Fischer, H., Liebigs Ann. Chem., 1990, 323; Kitagawa, O., Sato, T. and Taguchi, T., Chem. Lett., 1991, 177; Marek, I., Lefrancois, J. -M. and Normant, J. F., Tetrahedron Lett., 1992, 33, 1747.
6. 3. See for example: Bedford, S. B., Fenton, G., Knight, D. W. and Shaw, D. E., J. Chem. Soc., Perkin Trans 1, 1996, 1505; Ting, P. C and Bartlett, P. A., J. Am. Chem. Soc., 1984, 106, 2668; Tamura, Y., Hojo, M., Kawamura, Sawada, S., and Yoshida, Z., J. Org. Chem., 1987, 53, 4062; Maier, M. E., Kandler, H., Haller, B. U., Hoffman, J. H., and Fischer, H., Liebigs Ann. Chem., 1990, 323; Kitagawa, O., Sato, T. and Taguchi, T., Chem. Lett., 1991, 177; Marek, I., Lefrancois, J. -M. and Normant, J. F., Tetrahedron Lett., 1992, 33, 1747.
7. 3. See for example: Bedford, S. B., Fenton, G., Knight, D. W. and Shaw, D. E., J. Chem. Soc., Perkin Trans 1, 1996, 1505; Ting, P. C and Bartlett, P. A., J. Am. Chem. Soc., 1984, 106, 2668; Tamura, Y., Hojo, M., Kawamura, Sawada, S., and Yoshida, Z., J. Org. Chem., 1987, 53, 4062; Maier, M. E., Kandler, H., Haller, B. U., Hoffman, J. H., and Fischer, H., Liebigs Ann. Chem., 1990, 323; Kitagawa, O., Sato, T. and Taguchi, T., Chem. Lett., 1991, 177; Marek, I., Lefrancois, J. -M. and Normant, J. F., Tetrahedron Lett., 1992, 33, 1747.
8. 3. See for example: Bedford, S. B., Fenton, G., Knight, D. W. and Shaw, D. E., J. Chem. Soc., Perkin Trans 1, 1996, 1505; Ting, P. C and Bartlett, P. A., J. Am. Chem. Soc., 1984, 106, 2668; Tamura, Y., Hojo, M., Kawamura, Sawada, S., and Yoshida, Z., J. Org. Chem., 1987, 53, 4062; Maier, M. E., Kandler, H., Haller, B. U., Hoffman, J. H., and Fischer, H., Liebigs Ann. Chem., 1990, 323; Kitagawa, O., Sato, T. and Taguchi, T., Chem. Lett., 1991, 177; Marek, I., Lefrancois, J. -M. and Normant, J. F., Tetrahedron Lett., 1992, 33, 1747.
9. 3. See for example: Bedford, S. B., Fenton, G., Knight, D. W. and Shaw, D. E., J. Chem. Soc., Perkin Trans 1, 1996, 1505; Ting, P. C and Bartlett, P. A., J. Am. Chem. Soc., 1984, 106, 2668; Tamura, Y., Hojo, M., Kawamura, Sawada, S., and Yoshida, Z., J. Org. Chem., 1987, 53, 4062; Maier, M. E., Kandler, H., Haller, B. U., Hoffman, J. H., and Fischer, H., Liebigs Ann. Chem., 1990, 323; Kitagawa, O., Sato, T. and Taguchi, T., Chem. Lett., 1991, 177; Marek, I., Lefrancois, J. -M. and Normant, J. F., Tetrahedron Lett., 1992, 33, 1747.
10. 3. See for example: Bedford, S. B., Fenton, G., Knight, D. W. and Shaw, D. E., J. Chem. Soc., Perkin Trans 1, 1996, 1505; Ting, P. C and Bartlett, P. A., J. Am. Chem. Soc., 1984, 106, 2668; Tamura, Y., Hojo, M., Kawamura, Sawada, S., and Yoshida, Z., J. Org. Chem., 1987, 53, 4062; Maier, M. E., Kandler, H., Haller, B. U., Hoffman, J. H., and Fischer, H., Liebigs Ann. Chem., 1990, 323; Kitagawa, O., Sato, T. and Taguchi, T., Chem. Lett., 1991, 177; Marek, I., Lefrancois, J. -M. and Normant, J. F., Tetrahedron Lett., 1992, 33, 1747.
11. 4. Bartlett, P. A., Richardson, D. P. and Myerson, J., Tetrahedron, 1984, 40, 2317; Rychnovsky, S. D. and Bartlett, P. A., J. Am. Chem. Soc., 1981, 103, 3963.
12. 4. Bartlett, P. A., Richardson, D. P. and Myerson, J., Tetrahedron, 1984, 40, 2317; Rychnovsky, S. D. and Bartlett, P. A., J. Am. Chem. Soc., 1981, 103, 3963.
13. 5. Galatsis, P., Millan, S. D., Nechala, P. and Ferguson, J. Org. Chem., 1994, 59, 6643; Galatsis, P., Millan, S. D., and Ferguson, J. Org. Chem., 1997, 62, 5048.
14. 5. Galatsis, P., Millan, S. D., Nechala, P. and Ferguson, J. Org. Chem., 1994, 59, 6643; Galatsis, P., Millan, S. D., and Ferguson, J. Org. Chem., 1997, 62, 5048.
15. 6. Bedford, S. B., Bell, K. E., Fenton, G., Hayes, C. J., Knight, D. W. and Shaw, D., Tetrahedron Lett., 1992, 33, 6511; Barks, J. M., Knight, D. W. Seaman, C. J. and Weingarten, G. G, Tetrahedron Lett., 1994, 35, 7259; Barks, J. M., Knight, D. W. and Weingarten, G. G, J. Chem. Soc., Chem Commun., 1994, 719.
16. 6. Bedford, S. B., Bell, K. E., Fenton, G., Hayes, C. J., Knight, D. W. and Shaw, D., Tetrahedron Lett., 1992, 33, 6511; Barks, J. M., Knight, D. W. Seaman, C. J. and Weingarten, G. G, Tetrahedron Lett., 1994, 35, 7259; Barks, J. M., Knight, D. W. and Weingarten, G. G, J. Chem. Soc., Chem Commun., 1994, 719.
17. 6. Bedford, S. B., Bell, K. E., Fenton, G., Hayes, C. J., Knight, D. W. and Shaw, D., Tetrahedron Lett., 1992, 33, 6511; Barks, J. M., Knight, D. W. Seaman, C. J. and Weingarten, G. G, Tetrahedron Lett., 1994, 35, 7259; Barks, J. M., Knight, D. W. and Weingarten, G. G, J. Chem. Soc., Chem Commun., 1994, 719.
18. 7. Bartlett, P. A., Holm, K. H. and Morimoto, A., J. Org. Chem., 1985, 50, 5179.
19. 8. Bartlett P. A. and Myerson, J., J. Am. Chem. Soc., 1978, 100, 3950.
20. 9. Bennett, F., Bedford, S. B., Bell, K. E., Fenton, G., Knight, D. W. and Shaw, D., Tetrahedron Lett., 1992, 33, 6507.
21. 10. Kočovský, P and Tureček, F., Tetrahedron, 1983, 39, 3621.
22. 11. Gunther, H. J., Guntrum, E. and Jager, V., Liebigs Ann. Chem., 1984, 15.