Regio- and stereoselective ring opening of aziridines with nitric oxide

Tetrahedron Letters

Volumn 46, Issue 6, 2005, Pages 1023-1025

  Liu, Zhong Quan ^a   Fan, Yuan ^a   Li, Rui ^a   Zhou, Bo ^a   Wu, Long Min ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Aziridine; Nitric oxide; Ring opening

Indexed keywords

AZIRIDINE DERIVATIVE; NITRIC OXIDE;

ARTICLE; CHEMICAL REACTION KINETICS; QUANTUM YIELD; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY;

EID: 12344307252     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.011     Document Type: Article

References (24)

1. D. Tanner Angew. Chem., Int. Ed. Engl. 33 1994 599
2. H. Tamamura, M. Yamashita, H. Muramatsu, H. Ohno, T. Ibuka, A. Otaka, and N. Fujii Chem. Commun. 1997 2327
3. W.H. Pearson, and S.C. Bergmeier A. Padwa Comprehensive Heterocyclic Chemistry II Vol. 1A 1996 Pergamon Oxford 1 60
4. P. Golding, R.W. Millar, N.C. Paul, and D.H. Richards Tetrahedron 49 1993 7063
5. R.S. Atkinson, A.P. Ayscough, W.T. Gattrell, and T.M. Raynham Tetrahedron Lett. 39 1998 4377
6. For the important biological actions of nitric oxide, see: D.L.H. Williams Org. Biomol. Chem. 1 2003 441
7. S. Pfeiffer, B. Mayer, and B. Hemmens Angew. Chem., Int. Ed. 38 1999 1714
8. F. Murad Angew. Chem., Int. Ed. 38 1999 1856
9. R.F. Furchgott Angew. Chem., Int. Ed. 38 1999 1870
10. L.J. Ignarro Angew. Chem., Int. Ed. 38 1999 1882
11. For recent reviews, see: J.A. Hrabie, and L.K. Keefer Chem. Rev. 102 2002 1135
12. M. d'Ischia Tetrahedron Lett. 36 1996 8881
13. J.A. Hrabie, A. Srinivasan, C. George, and L.K. Keffer Tetrahedron Lett. 39 1998 5933
14. T. Itoh, K. Nagata, Y. Matsuga, M. Miyazaki, and A. Ohsawa Tetrahedron Lett. 38 1997 5017
15. T. Itoh, K. Nagata, Y. Matsuga, M. Miyazaki, and A. Ohsawa Tetrahedron Lett. 38 1997 4117
16. T. Sugihara, K. Kuwahara, A. Wakabayashi, H. Takao, H. Imagawa, and M. Nishizawa Chem. Commun. 2004 216
17. P.J. Gryglewski, R.M. Palmer, and S.A. Moncada Nature 320 1986 454
18. Z.-Q. Liu, R. Li, D.-S. Yang, and L.-M. Wu Tetrahedron Lett. 45 2004 1565
19. R. Boschan, R.T. Merrow, and R.W. Van Dolah Chem. Rev. 55 1955 485
20. J.F. Brown Jr. J. Am. Chem. Soc. 79 1957 2480
21. H.G. Korth, R. Sustmann, P. Lommes, T. Paul, A. Ernst, H. de Groot, L. Hughes, and K.U. Ingold J. Am. Chem. Soc. 116 1994 2767
22. D.R. Kelly, S. Jones, J.O. Adigum, K.S.V. Koh, D.E. Hibbs, M.B. Hursthouse, and S.K. Jackson Tetrahedron 53 1997 17221
23. W.A. Pryor, J.W. Lightsey, and D.F. Church J. Am. Chem. Soc. 104 1982 6685
24. For the synthesis of substrates, see: J.U. Jeong, B. Tao, I. Sagasser, H. Henniges, and K.B. Sharpless J. Am. Chem. Soc. 120 1998 6844