Regioselective and stereoselective glycidic oxirane ring opening: A new entry to optically pure α-alkyl α-hydroxy β-amino acid derivatives

Tetrahedron Letters

Volumn 41, Issue 28, 2000, Pages 5357-5361

  Garciía Ruano, Jose L ^a   García Paredes, Cristina ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; AMIDE; BETA AMINO ACID; ESTER; ETHYLENE OXIDE; OXAZOLINE DERIVATIVE;

ARTICLE; CATALYSIS; ENANTIOMER; HYDROLYSIS; HYDROXYLATION; REACTION ANALYSIS; REDUCTION; REPRODUCIBILITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0009909621     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039-(00)00842-X     Document Type: Article

References (36)

1. Nagai, M.; Kojima, F.; Naganawa, H.; Hamada, M.; Aoyagi, T.; Takeuchi, T. J. Antibiot. 1997, 50, 82 and references cited therein.
2. (a) Rubin, A. E.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2637.
3. (b) Keding, S. J.; Dales, N. A.; Lin, S.; Beaulieu, D.; Rich, D. H. Synth. Commun. 1998, 28, 4463.
4. Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377.
5. (a) Patel, R. N.; Banerjee, A.; Howell, J. M.; McNamee, C. G.; Brozozowski, D.; Mirfakhrae, D.; Nanduri, V.; Thottathil, J. K.; Szarka, L. J. Tetrahedron: Asymmetry 1993, 4, 2069.
6. (b) Kearns, J.; Kayser, M. M. Tetrahedron Lett. 1994, 35, 2845.
7. (c) Nozaki, K.; Sato, N.; Takaya, H. Tetrahedron: Asymmetry 1993, 4, 2179.
8. (d) Wasserman, H. H.; Xia, M.; Petersen, A. K.; Korgensen, M. R.; Curtis, E. A. Tetrahedron Lett. 1999, 40, 6163.
9. (a) Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181.
10. (b) Harihara, M.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 7570.
11. Nocioni, A. M.; Papa, C.; Tomasini, C. Tetrahedron Lett. 1999, 40, 8453.
12. Cardillo, G.; Tolomelli, A.; Tomasini, C. Eur. J. Org. Chem. 1999, 5, 155.
13. Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubel, W. D. Tetrahedron 1997, 53, 12789.
14. García Ruano, J. L.; Martín Castro, A. M.; Rodriguez Ramos, J. H.; Flamarique, A. C. R. Tetrahedron: Asymmetry 1997, 8, 3507
15. For reviews: (a) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (b) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837.
16. For reviews: (a) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (b) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837.
17. (a) Zhou, P.; Blubaum, J. E.; Burns, C. T.; Natale, N. R. Tetrahedron Lett. 1997, 38, 7019.
18. (b) Wipf, P.; Venkatraman, S. Tetrahedron Lett. 1996, 37, 4659.
19. (c) Vorbrüggen, H.; Krolikiewicz, K. Tetrahedron 1993, 49, 9353.
20. (a) Zhou, P.; Blubaum, J. E.; Burns, C. T.; Natale, N. R. Tetrahedron Lett. 1997, 38, 7019.
21. (b) Wipf, P.; Venkatraman, S. Tetrahedron Lett. 1996, 37, 4659.
22. (c) Vorbrüggen, H.; Krolikiewicz, K. Tetrahedron 1993, 49, 9353.
23. Guirado, A.; Andreu, R.; Gálvez, J. Tetrahedron Lett. 1998, 39, 1071 and references cited therein.
24. The oxirane opening with acetonitrile, catalysed by protic or Lewis acids, which in some cases is described to afford 2-oxazolines, has been reported (see: Bishop, R. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press. Oxford, 1991; Vol. 6, pp. 271 and 276 and references cited therein). Nevertheless, these reactions have been hardly used in synthesis (Kazi, A. B.; Shidmand, S.; Hajdu, J. J. Org. Chem. 1999, 64, 9337).
25. The oxirane opening with acetonitrile, catalysed by protic or Lewis acids, which in some cases is described to afford 2-oxazolines, has been reported (see: Bishop, R. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press. Oxford, 1991; Vol. 6, pp. 271 and 276 and references cited therein). Nevertheless, these reactions have been hardly used in synthesis (Kazi, A. B.; Shidmand, S.; Hajdu, J. J. Org. Chem. 1999, 64, 9337).
26. Catasús, M.; Moyano, A.; Pericás, M. A.; Riera, A. Tetrahedron Lett. 1999, 40, 9309 and references cited therein.
27. (a) Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 287.
28. (b) Chuang, T.-H.; Sharpless, K. B. Org. Lett. 1999, 1, 1435.
29. The use of microwaves facilitates these reactions (Lindström, U. M.; Olofsson, B.; Somfai, P. Tetrahedron Lett. 1999, 40, 9273).
30. 2.
31. 2 group.
32. Smith, J. R. L.; Norman, R. O. C.; Stirling, M. R. J. Chem. Soc., Perkin Trans. 1 1974, 1200.
33. Bickborn, B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p. 733.
34. Racemic glycidic esters 6-8 were obtained from the corresponding olefins by epoxidation with MCPBA and the optically pure 9 was prepared as indicated in Ref. 9.
35. Chloroform solutions of the oxazolines spontaneously evolved into the N-acetylamino hydroxy derivatives in one week at rt.
36. br, 2H), 4.20 (dq, J=6.8, 9.3 Hz, 1H), 2.24 (sep, J=6.5 Hz, 1H), 2.16 (s, 1H), 1.17 (d, J=6.8 Hz, 3H), 0.92 (d, J=6.8 Hz, 3H), 0.87 (d, J=6.8 Hz, 3H).