Two-Step Asymmetric Synthesis of Disubstituted N-Tosyl Aziridines Having 98-100% ee: Use of a Phosphazene Base

Journal of Organic Chemistry

Volumn 69, Issue 4, 2004, Pages 1409-1412

  Solladié Cavallo, Arlette ^c   Roje, Marin ^a   Welter, Richard ^b   Šunjić, Vitomir ^c  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

SALTS; STOICHIOMETRY; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

BIJVOET METHOD; HAZARDOUS REAGENTS;

AMINES;

ALKYL GROUP; AZIRIDINE DERIVATIVE; N TOSYLAZIRIDINE; PHOSPHATE; PHOSPHAZENE; SULFONIUM DERIVATIVE; TOSYLIMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; ENANTIOMER; STOICHIOMETRY; SUBSTITUTION REACTION; SYNTHESIS; X RAY ANALYSIS;

EID: 10744225951     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035586x     Document Type: Article

References (36)

1. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328-5329.
2. Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326-5327.
3. Sander, C. J.; Gillepsie, K. M.; Bell, D.; Scott, P. J. Am. Chem. Soc. 2000, 122, 7132-7133.
4. Nishikori, H.; Katsuki, T. Tetrahedron Lett. 1996, 37, 9245-9248.
5. Minakata, S.; Takeya, A.; Nishimura, M.; Ryu, I.; Komatsu, M. Angew. Chem., Int. Ed. 1998, 37, 3392-3394.
6. Jeong, J. U.; Tao, B.; Sagasser, I.; Hennigs, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844-6845.
7. Hansen, K. B.; Finney, N. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1995, 34, 676-678.
8. Rasmussen, K. G.; Jorgensen, K. A. J. Chem. Soc., Chem. Commun. 1995, 1401-1402.
9. Antilla, J. C.; Wulff, W. D. Angew. Chem., Int. Ed. 2000, 39, 4518-4521.
10. Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Sweeney, J. B. Chem. Commun. 1996, 2631-2632.
11. Garner, P.; Dogan, O.; Pillai, S. Tetrahedron Lett. 1994, 35, 1653-1656.
12. Cardillo, G.; Gentillucci, L.; Tomasini, C.; Castejon-Bordas, M. P. V. Tetrahedron: Asymmetry 1996, 7, 755-762.
13. Davis, F. A.; McCoull, W. Tetrahedron Lett. 1999, 40, 249-252.
14. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353-1364.
15. Li, A. H.; Zhou, Y. G.; Dai, L. X.; Hou, X. L.; Xia, L. J.; Lin, L. J. Org. Chem. 1998, 63, 4338-4348.
16. Aggarwal, V. K.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Org. Chem. 1996, 61, 8368-8369.
17. Saito, T.; Sakairi, M.; Akiba, D. Tetrahedron Lett. 2001, 42, 5451-5454.
18. Solladié-Cavallo, A.; Adib, A. Tetrahedron 1992, 48, 2453 and Solladié-Cavallo, A.; Diep-Vohuule, A. J. Org. Chem. 1995, 60, 3494-3498.
19. Solladié-Cavallo, A.; Adib, A. Tetrahedron 1992, 48, 2453 and Solladié-Cavallo, A.; Diep-Vohuule, A. J. Org. Chem. 1995, 60, 3494-3498.
20. Solladié-Cavallo, A.; Diep-Vohuule, A.; Šunjić, V.; Vinković, V. Tetrahedron: Asymmetry 1996, 7, 1783-1788.
21. Solladie-Cavallo, A.; Diep-Vohuule, A.; Isarno, T. Angew. Chem., Int. Ed. 1998, 37, 1689-1691.
22. Aggarwal, V. K.; Charmant, J. P. H.; Ciampi, C.; Hornby, J. M.; O'Brien, C. J.; Hind, G.; Parsons, R. J. Chem. Soc., Perkin Trans. 1 2001, 3159-3166.
23. Aggarwal, V. K.; Ferrara, M.; O'Brien, C. J.; Thompson, A.; Jones, R. V. H.; Fieldhouse, R. J. Chem. Soc., Perkin Trans. 1 2001, 1635-1643.
24. Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hind, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433-1436.
25. Solladié-Cavallo, A.; Adib, A.; Schmitt, M.; Fischer, J.; DeCian, A. Tetrahedron: Asymmetry 1992, 3, 1597-1602.
26. Vedejs, E.; Engler, D. A.; Mullins, M. J. J. Org. Chem. 1977, 42, 3109-3113.
27. Solladié-Cavallo, A.; Roje, M.; Isarno, T.; Šunji, V.; Vinković, V. Eur. J. Org. Chem. 2000, 1077-1080.
28. CH(Ph) δ in ppm. 1-trans = 4.39; 1-cis = 4.48; 2-trans = 4.38; 2-cis = 4.54; 3-trans = 4.34; 3-cis = 4.46; 4-trans = 3.80; 4-cis = 3.94; 5-trans = 3.78; 5-cis = 3.98; 6-trans = 4.26; 6-cis = 4.22; 7-trans = 4.28; 7-cis = 4.34; 8-trans = 4.19; 8-cis = 4.33.
29. Eliel, E. L.; Wilen, S. H.; Mander, L. N. In Stereochemistry of Organic Compounds; John Wiley & Sons, Inc.: New York, 1994; pp 113-114.
30. Conformation K1 corresponds to the only conformation populated of the starting sulfonium salt 9 (cf. ref 18), which is obviously also the more reactive.
31. Aggarwal, V. K.; Calamai, S.; Ford, J. G. J. Chem. Soc., Perkin Trans. 1 1997, 593-600.
32. Isarno, T., Ph.D., Strasbourg-France, 2000. Alkyl-phenyl epoxides are obtained as trans/cis mixture either as a result of smaller differences between the rates of ring closure or less reversible betaines formation.
33. For discussion on anti approach and ring closing or syn approach, followed by C-C rotation and then ring closing, see: Volatron, F.; Eisenstein, O. J. Am. Chem. Soc. 1987, 109, 1-14.
34. Sheldrick, G. M. SHELXL97, program for the refinement of crystal structures; University of Gottingen: Germany, 1997.
35. Welter, R.; Romang, J. F. CRYSTALBUILDER-GUI for SHELXL97 on MACOSX; Louis Pasteur University-Strasbourg: Fance, 2002.
36. Flack, H. D. Acta Crystallogr. A39, 1983, 876-881.