Easy and efficient synthesis of enantiomerically enriched 2H-azirines derived from phosphonates

Tetrahedron Letters

Volumn 41, Issue 28, 2000, Pages 5363-5366

  Palacios, Francisco ^a   Ochoa de Retana, Ana M ^a   Gil, José I ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Aminophosphonates; Asymmetric synthesis; Aziridines; Azirines; Oximes; Phosphonates

Indexed keywords

AZIRIDINE DERIVATIVE; AZIRINE DERIVATIVE; FOSFOMYCIN; OXIME; PHOSPHONIC ACID DERIVATIVE; SODIUM BOROHYDRIDE;

ARTICLE; ENANTIOMER; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; STOICHIOMETRY; SYNTHESIS;

EID: 0034622355     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00843-1     Document Type: Article

References (35)

1. For reviews on azirines, see: (a) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 1, pp. 1-60. (b) Backes, J. In Methoden der Organische Chemie (Houben-Weyl); Thieme, G., Eds.; Stuttgart, 1992; Vol. E16c; pp. 317-369.
2. For reviews on azirines, see: (a) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 1, pp. 1-60. (b) Backes, J. In Methoden der Organische Chemie (Houben-Weyl); Thieme, G., Eds.; Stuttgart, 1992; Vol. E16c; pp. 317-369.
3. (a) Davis, F. A.; Liu, H.; Zhou, P.; Fang, T. V.; Reddy, G. V.; Zhang, Y. L. J. Org. Chem. 1999, 64, 7559-7567.
4. (b) Albrecht, E.; Mattay, J.; Steenken, S. J. Am. Chem. Soc. 1997, 119, 11605-11610.
5. (a) Miller, T. M.; Tristram, E. W.; Wolf, F. J. J. Antibiot. 1971, 24, 48-50.
6. (b) Molinski, T. F.; Ireland, C. M. J. Org. Chem. 1988, 53, 2103-2105.
7. (c) Salomon, C. E.; William, D. H.; Faulkner, D. J. J. Nat. Prod. 1995, 58, 1463-1466.
8. For reviews, see: (a) Engel, R. In Handbook of Organophosphorus Chemistry; Dekker, M. Inc.: New York, 1992. (b) Kafarski, P.; Lejezak, B. Phosphorus & Sulfur 1991, 63, 193-215.
9. For reviews, see: (a) Engel, R. In Handbook of Organophosphorus Chemistry; Dekker, M. Inc.: New York, 1992. (b) Kafarski, P.; Lejezak, B. Phosphorus & Sulfur 1991, 63, 193-215.
10. (a) Allenberger, F.; Klare, Y. J. Antimicrob. Chemother. 1999, 43, 211-217.
11. (b) Kawakami, Y.; Furuwatari, C.; Akahane, T.; Okimura, Y.; Fusihata, K.; Katsuyama, T.; Matsumoto, H. J. Antibiot. 1994, 47, 507-510.
12. (c) Tsuboi, T.; Ida, H.; Yoshikawa, E.; Hiyoshi, S.; Yamagi, E.; Nakayama, Y.; O'Hara, K.; Nonomiya, T.; Shigenobu, F.; Toniguchi, K.; Shimizu, M.; Sawai, T.; Mizuokowa, K. Clin. Chim. Acta 1999, 279, 175-179.
13. (a) Smith, A. B.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1995, 117, 10879-10888.
14. (b) Hirschmann, R.; Smith, A. B.; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Spengler, P. A.; Benkovic, S. J. Science 1994, 265, 234-237.
15. (c) Meyer, J. H.; Bartlett, P. A. J. Am. Chem. Soc. 1998, 120, 4600-4609.
16. (d) Smith, A. B.; Yager, K. M.; Taylor, C. M. PCT Int. Appl. WO 95 25,11, 1995; Chem. Abstr. 1996, 124, 87370.
17. (a) Davis, F. A.; Liu, H.; Liang, C.; Reddy, G. V.; Zhang, Y.; Fang, T.; Titus, D. D. J. Org. Chem. 1999, 64, 8929-8935;
18. (b) Davis, F. A.; Reddy, G. V.; Liu, H. J. Am. Chem. Soc. 1995, 117, 3651-3652.
19. (c) Gentillucci, L.; Grijzen, Y.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1995, 36, 4665-4668.
20. (d) Verstappen, M. M. H.; Arians, G. J. A.; Zwanenburg, B. J. Am. Chem. Soc. 1996, 118, 8491-8492.
21. (e) Piskunova, I. P.; Eremeev, A. V.; Mishnev, A. F.; Vosekalna, I. A. Tetrahedron 1993, 49, 4671-4676.
22. (a) Alcaraz, G.; Wecker, U.; Baceiredo, A.; Dahan, F.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1246-1248.
23. (b) Piquet, V.; Baceiredo, A.; Gornitzka, H.; Dahan, F.; Bertrand, G. Chem. Eur. J. 1997, 3, 1757-1264.
24. (c) Davis, F. A.; McCoull, W. Tetrahedron Lett. 1999, 40, 249-252.
25. (a) Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1999, 55, 13767-13778.
26. (b) Palacios, F.; Ochoa de Retana, A.; Oyarzabal, J. Tetrahedron 1999, 55, 5947-5964.
27. (c) Palacios, F.; Gil, M. J.; Martínez, E.; Rodríguez, M. Tetrahedron Lett. 1999, 40, 2411-2414.
28. (a) Neber, P. W.; Burghard, A. Justus Liebigs Ann. Chem. 1932, 493, 281-294.
29. (b) McCarthy, C. G. In The Chemistry of the Carbon-Nitrogen Bond; Patai, S., Ed.; Interscience: New York, 1973; pp. 447-452.
30. Palacios, F.; Aparicio, D.; de los Santos, J. M.; Rodríguez, E. Tetrahedron 1998, 54, 599-614.
31. Duggan, M. E.; Karanewsky, D. S. Tetrahedron. Lett. 1983, 24, 2935-2938.
32. (a) Thomas, A. A.; Sharpless, K. B. J. Org. Chem. 1999, 64, 8379-8385;
33. (b) Hori, K.; Sugihara, H.; Ito, Y. N.; Katsubi, T. Tetrahedron Lett. 1999, 40, 5207-5210.
34. (a) Chandrasekhar, S.; Ahmed, M. Tetrahedron Lett. 1999, 40, 9325-9327.
35. (c) Davis, F. A.; Zhou, P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243-3245.