Enantioselective addition of Grignard reagents to a 2-thiazolyl nitrone

Tetrahedron Asymmetry

Volumn 7, Issue 3, 1996, Pages 667-670

  Merchán, Francisco L ^a   Merino, Pedro ^a   Rojo, Isabel ^a   Tejero, Tomas ^a   Dondoni, Alessandro ^b  

^a CSIC   (Spain)

^b UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

THIAZOLE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029928097     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00060-2     Document Type: Article

References (36)

1. (a) Soai, K.; Niwa, S. Chem. Rew. 1992, 92, 833-856.
2. (b) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 6117-6128.
3. (c) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995, ch. 6.
4. Review : Johansson, A. Contemp. Org. Synth. 1995, 393-407. Recent papers :
5. (b) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron: Asymm. 1993, 4, 1603-1606.
6. (c) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron: Asymm. 1995, 6, 2527-2533.
7. (d) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797-8798.
8. (e) Soai, K.; Suzuki, T.; Shono, T. J. Chem. Soc. Chem. Commun. 1994, 317-318.
9. (f) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429-4438.
10. (g) Jones, C. A.; Jones, I. G.; North, M.; Pool. C. R. Tetrahedron Lett. 1995, 36, 7885-7888.
11. (a) Cicchi, S.; Hold, I.; Brandi, A. J. Org. Chem. 1993, 58, 5274-5275.
12. (b) Giovannini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1995, 60, 5706-5707.
13. (a) Huber, R.; Vasella, A. Tetrahedron 1990, 46, 33-58.
14. (b) Chang, Z. Y.; Coates, R. M. J. Org. Chem. 1990, 55, 3464-3474 and 3475-3483.
15. (c) Rohloff, J. C.; Alfredson, T. V.; Schwartz, M. A. Tetrahedron Lett. 1994, 35, 1011-1014.
16. (d) Basha, A.; Henry, R.; McLaughlin, M. A.; Ratajczyh, J. D.; Wittenberger, S. J. J. Org. Chem. 1994, 59, 6103-6106.
17. (a) Dondoni, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Synthesis 1994, 1450-1456.
18. (b) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Chem. Eur. J. 1995, 1, 101-116 and references therein.
19. Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313-1316. There are also report on the enantioselective hydrogenation of nitrones (see Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703-11714), enantioselective deprotonation (see Willems, J. G. H.; de Vries, J. G.; Nolte, R. J. M.; Zwanenburg, B. Tetrahedron Lett. 1995, 36, 3917-3920) and enantioselective 1,3-dipolar cycloadditions (see Seerden, J.-P. G.; Kuypers, M. M. M.; Scheeren, H. W. Tetrahedron: Asymm. 1995, 6, 1441-1450 and Seerden, J.-P. G.; Scholte op Reimer, A. W. A.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 4419-4422.
20. Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313-1316. There are also report on the enantioselective hydrogenation of nitrones (see Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703-11714), enantioselective deprotonation (see Willems, J. G. H.; de Vries, J. G.; Nolte, R. J. M.; Zwanenburg, B. Tetrahedron Lett. 1995, 36, 3917-3920) and enantioselective 1,3-dipolar cycloadditions (see Seerden, J.-P. G.; Kuypers, M. M. M.; Scheeren, H. W. Tetrahedron: Asymm. 1995, 6, 1441-1450 and Seerden, J.-P. G.; Scholte op Reimer, A. W. A.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 4419-4422.
21. Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313-1316. There are also report on the enantioselective hydrogenation of nitrones (see Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703-11714), enantioselective deprotonation (see Willems, J. G. H.; de Vries, J. G.; Nolte, R. J. M.; Zwanenburg, B. Tetrahedron Lett. 1995, 36, 3917-3920) and enantioselective 1,3-dipolar cycloadditions (see Seerden, J.-P. G.; Kuypers, M. M. M.; Scheeren, H. W. Tetrahedron: Asymm. 1995, 6, 1441-1450 and Seerden, J.-P. G.; Scholte op Reimer, A. W. A.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 4419-4422.
22. Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313-1316. There are also report on the enantioselective hydrogenation of nitrones (see Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703-11714), enantioselective deprotonation (see Willems, J. G. H.; de Vries, J. G.; Nolte, R. J. M.; Zwanenburg, B. Tetrahedron Lett. 1995, 36, 3917-3920) and enantioselective 1,3-dipolar cycloadditions (see Seerden, J.-P. G.; Kuypers, M. M. M.; Scheeren, H. W. Tetrahedron: Asymm. 1995, 6, 1441-1450 and Seerden, J.-P. G.; Scholte op Reimer, A. W. A.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 4419-4422.
23. Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313-1316. There are also report on the enantioselective hydrogenation of nitrones (see Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703-11714), enantioselective deprotonation (see Willems, J. G. H.; de Vries, J. G.; Nolte, R. J. M.; Zwanenburg, B. Tetrahedron Lett. 1995, 36, 3917-3920) and enantioselective 1,3-dipolar cycloadditions (see Seerden, J.-P. G.; Kuypers, M. M. M.; Scheeren, H. W. Tetrahedron: Asymm. 1995, 6, 1441-1450 and Seerden, J.-P. G.; Scholte op Reimer, A. W. A.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 4419-4422.
24. Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synth. Commun. 1994, 24, 2537-2550.
25. (a) Pettit, G. R.; Kamano, Y.; Herald, C. L.; Tuinman, A. A.; Boettner, F. E.; Kizu, H.; Schmidt, J. M.; Baczynskyj, L.; Tomer, K. B.; Bontems, R. J. J. Am. Chem. Soc., 1987, 109, 6883-6885.
26. (b) Pettit, G. R.; Singh, S. B.; Hogan, F.; Lloyd-Williams, P.; Herald, D. L.; Burkett, D. D.; Clewlow, P. J. J. Am. Chem. Soc., 1989, 111, 5463-6465.
27. (c) Unson, M. D.; Rose, C. B.; Faulkner, D. J.; Brinen, L. S.; Steiner, J. R.; Clardy, J. J. Org. Chem., 1993, 58, 6336-6334.
28. For overviews on the "thiazole-aldehyde synthesis" see: (a) Dondoni, A. In Modern Synthetic Methods; Scheffold, R., Ed.; Verlag Helvetica Chimica Acta: Basel, 1992, pp 377-437.
29. (b) Dondoni, A. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, and VCH: Weinheim, 1992, pp 105-128.
30. 2O and DME; in toluene the reaction was unselective at all.
31. 2OSZn.
32. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-.
33. Merchan, F. L.; Merino, P.; Rojo, I.; Tejero, T.; Dondoni, A. Tetrahedron: Asymm. 1995, 6, 2145-2148.
34. Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron 1992, 48, 7251-7264
35. a) Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron: Asymm. 1995, 6, 12721-12744.
36. b) Dondoni, A.; Merchan, F. L.; Merino, P.; Rojo, I.; Tejero, T. Synthesis 1996, in press.