Preparation and Ring-Opening Reactions of N-Diphenylphosphinyl Vinyl Aziridines

Synlett

Volumn 1996, Issue 9, 1996, Pages 847-849

  Cantrill, Alex A ^a   Jarvis, Ashley N ^a   Osborn, Helen M I ^a   Ouadi, Ali ^a   Sweeney, J B ^a,b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002462212     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5605     Document Type: Article

References (23)

1. See, for instance, Tanner. D.; Almario, A.; Hogberg, T. Tetrahedron, 1995, 51, 6061 and references therein.
2. Yamada, Y.; Yamamoto, T.; Okawara, M. Chem. Lett., 1975, 361.
3. Evans, D.A.; Faul, M.M.; Bilodeau, M.T.; Anderson B.A.; D.M. Barnes J. Am. Chem. Soc., 1993, 115, 5328.
4. Li, Z.; Conser K.R.; Jacobsen, E.N. J. Am. Chem. Soc., 1993, 115, 5326.
5. Hansen, K.B.; Finney N.S.; Jacobsen, E.N. Angew. Chem., Int. Ed. Engl., 1995, 34, 676; Rasmussen K..G; Jorgensen, K.A. J. Chem. Soc., Chem. Commun., 1995, 1401. For a related process, see: Aggarwal, V.K.; Abdelrahman, H.; Thompson, A.; Mattison, B.; Jones, R.V.H Phosphorus, Sulfur, Silicon And Related Elements, 1994, 95, 283.
6. Hansen, K.B.; Finney N.S.; Jacobsen, E.N. Angew. Chem., Int. Ed. Engl., 1995, 34, 676; Rasmussen K..G; Jorgensen, K.A. J. Chem. Soc., Chem. Commun., 1995, 1401. For a related process, see: Aggarwal, V.K.; Abdelrahman, H.; Thompson, A.; Mattison, B.; Jones, R.V.H Phosphorus, Sulfur, Silicon And Related Elements, 1994, 95, 283.
7. Hansen, K.B.; Finney N.S.; Jacobsen, E.N. Angew. Chem., Int. Ed. Engl., 1995, 34, 676; Rasmussen K..G; Jorgensen, K.A. J. Chem. Soc., Chem. Commun., 1995, 1401. For a related process, see: Aggarwal, V.K.; Abdelrahman, H.; Thompson, A.; Mattison, B.; Jones, R.V.H Phosphorus, Sulfur, Silicon And Related Elements, 1994, 95, 283.
8. Li, A.-H.; Dai, X.-L.; Hou, X.-L, J. Chem. Soc., Chem. Commun., 1996, 491.
9. Mauzé, B. J. Organomet. Chem., 1980, 202, 233.
10. Cantrill, A.A.; Sweeney, J. B. Synlett, 1995, 1277; Cantrill, A.A.; Osborn, H.M.I.; Sweeney, J.B.; Howson, W. Tetrahedron Letters, 1994, 35, 3159; Osborn, H.M.I.; Sweeney, J.B.; Howson, W. Tetrahedron Letters, 1994, 35, 2739; Osborn, H. M. I.; Sweeney, J.B.; Howson, W. SynLett, 1994, 145.
11. Cantrill, A.A.; Sweeney, J. B. Synlett, 1995, 1277; Cantrill, A.A.; Osborn, H.M.I.; Sweeney, J.B.; Howson, W. Tetrahedron Letters, 1994, 35, 3159; Osborn, H.M.I.; Sweeney, J.B.; Howson, W. Tetrahedron Letters, 1994, 35, 2739; Osborn, H. M. I.; Sweeney, J.B.; Howson, W. SynLett, 1994, 145.
12. Cantrill, A.A.; Sweeney, J. B. Synlett, 1995, 1277; Cantrill, A.A.; Osborn, H.M.I.; Sweeney, J.B.; Howson, W. Tetrahedron Letters, 1994, 35, 3159; Osborn, H.M.I.; Sweeney, J.B.; Howson, W. Tetrahedron Letters, 1994, 35, 2739; Osborn, H. M. I.; Sweeney, J.B.; Howson, W. SynLett, 1994, 145.
13. Cantrill, A.A.; Sweeney, J. B. Synlett, 1995, 1277; Cantrill, A.A.; Osborn, H.M.I.; Sweeney, J.B.; Howson, W. Tetrahedron Letters, 1994, 35, 3159; Osborn, H.M.I.; Sweeney, J.B.; Howson, W. Tetrahedron Letters, 1994, 35, 2739; Osborn, H. M. I.; Sweeney, J.B.; Howson, W. SynLett, 1994, 145.
14. Mallaiah, K.; Satyanarayana, J.; Ila H.; Junjappa, H. Tetrahedron Lett., 1993, 34, 3145.
15. 21NOP requires 346.1361. Coupling constants were used to determine the relative stereochemistry. Upon irradiation of the resonance due to the benzylic CH, an nOe enhancement of 33% at the resonance due to the allylic CH was observed for the minor isomer, compared to an enhancement of only 8% for the major isomer, indicating presence of the trans-product and reinforcing the original assignment.
16. The ring-opening of 2-(carboxyvinyl)aziridines has been reported: Wipf, P.; Fritch, P.C; J. Org. Chem., 1994, 59, 4875; Satake, A.; Shimizu, I.; Yamamoto, A. Syntett, 1995, 64; Fujii, N.; Nakai, K.; Tamamura, K. H.; Otaka, A.; Mimura, N.; Miwa, Y.; Taga, T.; Yamamoto, Y.; Ibuka, T.J. Chem. Soc., Perkin Trans. 1, 1995, 1359; Ibuka, J.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849.
17. The ring-opening of 2-(carboxyvinyl)aziridines has been reported: Wipf, P.; Fritch, P.C; J. Org. Chem., 1994, 59, 4875; Satake, A.; Shimizu, I.; Yamamoto, A. Syntett, 1995, 64; Fujii, N.; Nakai, K.; Tamamura, K. H.; Otaka, A.; Mimura, N.; Miwa, Y.; Taga, T.; Yamamoto, Y.; Ibuka, T.J. Chem. Soc., Perkin Trans. 1, 1995, 1359; Ibuka, J.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849.
18. The ring-opening of 2-(carboxyvinyl)aziridines has been reported: Wipf, P.; Fritch, P.C; J. Org. Chem., 1994, 59, 4875; Satake, A.; Shimizu, I.; Yamamoto, A. Syntett, 1995, 64; Fujii, N.; Nakai, K.; Tamamura, K. H.; Otaka, A.; Mimura, N.; Miwa, Y.; Taga, T.; Yamamoto, Y.; Ibuka, T.J. Chem. Soc., Perkin Trans. 1, 1995, 1359; Ibuka, J.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849.
19. The ring-opening of 2-(carboxyvinyl)aziridines has been reported: Wipf, P.; Fritch, P.C; J. Org. Chem., 1994, 59, 4875; Satake, A.; Shimizu, I.; Yamamoto, A. Syntett, 1995, 64; Fujii, N.; Nakai, K.; Tamamura, K. H.; Otaka, A.; Mimura, N.; Miwa, Y.; Taga, T.; Yamamoto, Y.; Ibuka, T.J. Chem. Soc., Perkin Trans. 1, 1995, 1359; Ibuka, J.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849.
20. 25NOP requires 362.1674.
21. Piers, E.; Chong, J.M; Morton, H.E. Tetrahedron, 1989, 45, 363.
22. 1H nmr spectroscopy.
23. 4 according to: Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc., 1973, 95, 2697.