Highly stereoselective syn-ring opening of enantiopure epoxides with nitric oxide

Tetrahedron Letters

Volumn 48, Issue 9, 2007, Pages 1653-1656

  Wu, Wentao ^a   Liu, Qiang ^a   Shen, Yinglin ^a   Li, Rui ^a   Wu, Longmin ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 GLYCOL DERIVATIVE; EPOXIDE; GLYCOL; NITRIC ACID DERIVATIVE; NITRIC OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; REACTION ANALYSIS; REDUCTION; RING OPENING; STEREOCHEMISTRY;

EID: 33846629511     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.095     Document Type: Article

References (31)

1. Brown Jr. J.F. J. Am. Chem. Soc. 79 (1957) 2480-2488
2. Tuaillon J., and Perrot R. Helv. Chim. Acta 61 (1978) 558-566
3. Kelly D.R., Jones S., Adigun J.O., Koh K.S.V., Hibbs D.E., Hursthouse M.B., and Jackson S.K. Tetrahedron 53 (1997) 17221-17234
4. Park J.S.B., and Walton J.C. J. Chem. Soc., Perkin Trans. 2 (1997) 2579-2583
5. Hata E., Yamada T., and Mukaiyama T. Bull. Chem. Soc. Jpn. 68 (1995) 3629-3636
6. Drago R.S., and Paulk F.E. J. Am. Chem. Soc. 82 (1960) 96-98
7. Itoh T., and Nagata A. J. Org. Chem. 62 (1997) 3582-3585
8. Itoh T., Nagata K., Matsuya Y., Miyazaki M., and Ohsawa A. Tetrahedron Lett. 38 (1997) 5017-5020
9. Hrabie J.A., Arnold E.V., Citro M.L., George C., and Keefer L.K. J. Org. Chem. 65 (2000) 5745-5751
10. Danzig M.J., Martel R.F., and Riccitiello S.R. J. Org. Chem. 25 (1960) 1071-1072
11. Mao Y.Z., Liu Z.Q., and Wu L.M. Chin. J. Chem. 18 (2000) 789-791
12. Itoh T., Nagata K., Matsuya Y., Miyazaki M., and Ohsawa A. Tetrahedron Lett. 38 (1997) 4117-4120
13. Yang D.S., Lei L.D., Liu Z.Q., and Wu L.M. Tetrahedron Lett. 44 (2003) 7245-7247
14. Liu Z.Q., Li R., Yang D.S., and Wu L.M. Tetrahedron Lett. 45 (2004) 1565-1566
15. Liu Z.Q., Fan Y., Li R., Zhou B., and Wu L.M. Tetrahedron Lett. 46 (2005) 1023-1025
16. Fan Y., Shang X.J., Liu Z.Q., and Wu L.M. Synth. Commun. 36 (2006) 3149-3152
17. Fabio R.D., Russi T., and Thomas R.J. Tetrahedron Lett. 38 (1997) 3587-3590
18. Iranpoor N., and Salehi P. Tetrahedron 51 (1995) 909-912
19. The starting epoxides were prepared from the corresponding olefins using Shi's method. Wang Z.X., Tu Y., Frohn M., Zhang J.R., and Shi Y. J. Am. Chem. Soc. 119 (1997) 11224-11235
20. 4 (259): C, 64.86; H, 5.02; N, 5.41. Found: C, 64.59; H, 4.64; N, 5.42.
21. Boschan R., Merrow R.T., and Van Dolah R.W. Chem. Rev. 55 (1955) 485-510
22. Baker J.W., and Heggs T.G. Chem. Ind. (1954) 464
23. Nicols P.L., Magnasson A.B., and Ingham J.O. J. Am. Chem. Soc. 75 (1953) 4255-4258
24. Marans N.S., and Zelinski R.P. J. Am. Chem. Soc. 72 (1950) 5330-5331
25. Iranpoor N., Firouzobadi H., and Shekamiz M. Org. Biomol. Chem. 1 (2003) 724-727
26. Merrow R.T., and Van Dolah R.W. J. Am. Chem. Soc. 77 (1955) 756-757
27. Soffer L.M., Parrotta E.W., and Domenico J.D. J. Am. Chem. Soc. 74 (1952) 5301-5303
28. Merrow R.T., and Van Dolah R.W. J. Am. Chem. Soc. 76 (1954) 4522-4525
29. +, 0.4), 165 (1.3), 152 (0.7), 107 (100.0); ee >99%, dr >99:1 [HPLC, Chiralcel OJ-H column, hexane/2-propanol, 90:10, v/v, the flow rate, 0.8 mL/min].
30. Shen Y.L., Wu W.T., Liu Q., Wu G.L., and Wu L.M. J. Chem. Res. (2006) 545-546
31. Berti G., and Bottari F. J. Org. Chem. 25 (1960) 1286-1292