Ring-closing metathesis and ring-closing metathesis-isomerisation approach to 1-phosphonylated 2-benzazocines

Tetrahedron

Volumn 64, Issue 19, 2008, Pages 4295-4303

  Dieltiens, Nicolai ^a   Stevens, Christian V ^a   Masschelein, Kurt ^a   Hennebel, Geert ^a   Van der Jeught, Sarah ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZAZOCINE DERIVATIVE; BENZAZOCINE DERIVATIVE; PHOSPHORAMIDIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONE POT SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL; RING CLOSING METATHESIS;

EID: 41549106574     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.074     Document Type: Article

References (50)

1. Horton D.A., Bourne G.T., and Smythe M.L. Chem. Rev. 103 (2003) 893-930
2. Grunewald G.L., Dahanukar V.H., Ching P., and Criscione K.R. J. Med. Chem. 39 (1996) 3539-3546
3. For general reviews on RCM, see:
4. Schmalz H.-G. Angew. Chem., Int. Ed. Engl. 34 (1995) 1833-1836
5. Schuster M., and Blechert S. Angew. Chem., Int. Ed. 36 (1997) 2036-2056
6. Dragutan I., Dragutan V., and Filip P. Arkivoc x (2005) 105-129
7. Fürstner A. Angew. Chem., Int. Ed. 39 (2000) 3012-3043
8. Grubbs R.H., and Chang S. Tetrahedron 54 (1998) 4413-4450
9. Drozdzak R., Allaert B., Ledoux N., Dragutan I., Dragutan V., and Verpoort F. Coord. Chem. Rev. 249 (2005) 3055-3074
10. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4490-4527
11. Colacino E., Martinez J., and Lamaty F. Coord. Chem. Rev. 251 (2007) 726-764
12. For a review on the synthesis of oxygen- and nitrogen-containing heterocycles by RCM, see:. Deiters A., and Martin S.F. Chem. Rev. 104 (2004) 2199-2238
13. For a review on the synthesis of phosphorus and sulfur heterocycles by RCM, see:. McReynolds M.D., Dougherty J.M., and Hanson P.R. Chem. Rev. 104 (2004) 2239-2258
14. Dieltiens N., and Stevens C.V. Synlett (2006) 2771-2776
15. See the following review and articles cited therein:. Schmidt B., and Hermanns J. Curr. Org. Chem. 10 (2006) 1363-1396
16. Miller S.J., Kim S.-H., Cheng Z.-R., and Grubbs R.H. J. Am. Chem. Soc. 117 (1995) 2108-2109
17. Martin S.F., and Wagman A.S. Tetrahedron Lett. 36 (1995) 1169-1170
18. Martin S.F., Chen H.-J., Courtney A.K., Liao Y., Patzel M., Ramser M.N., and Wagman A.S. Tetrahedron 52 (1996) 7251-7264
19. Fellows I.M., Kaelin Jr. D.E., and Martin S.F. J. Am. Chem. Soc. 122 (2000) 10781-10787
20. Voskressensky L.G., Borisova T.N., Listratova A.V., Kulikova L.N., Titov A.A., and Varlamov A.V. Tetrahedron Lett. 47 (2006) 4585-4589
21. Panayides J.-L., Pathak R., Panagiotopoulos H., Davids H., Fernandes M.A., de Koning C.B., and van Otterlo W.A.L. Tetrahedron 63 (2007) 4737-4747
22. Sato S., Tanioka A., Ikeda M., and Izawa S. Bioorg. Med. Chem. 13 (2005) 5717-5732
23. Sato S., Tanioka A., Ikeda M., and Izawa S. Bioorg. Med. Chem. Lett. 15 (2005) 1479-1484
24. Sato S. Tetrahedron Lett. 45 (2004) 8475-8478
25. Moonen K., Dieltiens N., and Stevens C.V. J. Org. Chem. 71 (2006) 4006-4009
26. Dieltiens N., Moonen K., and Stevens C.V. Chem.-Eur. J. 13 (2007) 203-214
27. Moonen K., and Stevens C.V. Synthesis (2005) 3603-3612
28. Dieltiens N., and Stevens C.V. Org. Lett. 9 (2007) 465-468
29. Vanderhoydonck B., and Stevens C.V. Tetrahedron 63 (2007) 7679-7689
30. Moonen K., Laureyn I., and Stevens C.V. Chem. Rev. 104 (2004) 6177-6215
31. Azizi N., and Saidi M.R. Tetrahedron 59 (2003) 5329-5332
32. This reaction is based on a micro-wave synthesis:. Saulnier M.G., Zimmerman K., Struzynski C., Sang X., Velaparthi U., Wittman M., and Frennesson D. Tetrahedron Lett. 45 (2004) 397-399
33. Hartman G.D., Halczenko W., and Phillips B.T. J. Org. Chem. 50 (1985) 2427-2431
34. Scholl M., Ding S., Lee C.W., and Grubbs R.H. Org. Lett. 1 (1999) 953-956
35. Alcaide B., and Almendros P. Chem.-Eur. J. 9 (2003) 1259-1262
36. For an excellent review on metathesis/hydrogenation tandem reactions, see:. Schmidt B. Eur. J. Org. Chem. (2004) 1865-1880
37. In previous work we attributed oxidative dehydrogenation of pyrrolines to pyrroles to decomposition products of the second generation Grubbs' catalyst, see:. Dieltiens N., Stevens C.V., De Vos D., Allaert B., Drozdzak R., and Verpoort F. Tetrahedron Lett. 45 (2004) 8995-8998
38. Krompiec S., Kuznic N., Bieg T., Adamus B., Majnusz J., and Grymel M. Pol. J. Chem. 74 (2000) 1197-1200
39. Krompiec S., Pigulla M., Bieg T., Szczepankiewicz W., Kuznic N., Krompiec M., and Kubicki M. J. Mol. Catal. A 189 (2002) 169-185
40. van Otterlo W.A.L., Ngidi E.L., and de Koning C.B. Tetrahedron Lett. 44 (2003) 6483-6486
41. van Otterlo W.A.L., Morgans G.L., Khanye S.D., Aderibigde B.A.A., Michael J.P., and Billing D.G. Tetrahedron Lett. 45 (2004) 9171-9175
42. van Otterlo W.A.L., Morgans G.L., Madeley L.G., Kuzvidza S., Moleele S.S., Thornton N., and de Koning C.B. Tetrahedron 61 (2005) 7746-7755
43. Trnka T.M., Morgan J.P., Sanford M.S., Wilhelm T.E., Scholl M., Choi T.-L., Ding S., Day M.W., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 2546-2558
44. Hong S.H., Day M.W., and Grubbs R.H. J. Am. Chem. Soc. 126 (2004) 7414-7415
45. Drouin S.D., Yap G.P.A., and Fogg D.E. Inorg. Chem. 39 (2000) 5412-5414
46. Fustero S., Sanchez-Rosello M., Jimenez D., Sanz-Cervera J.F., del Pozo C., and Acena J.L. J. Org. Chem. 71 (2006) 2706-2714
47. Schwab P., France M.B., Ziller J.W., and Grubbs R.H. Angew. Chem., Int. Ed. Engl. 34 (1995) 2039-2041
48. Sanford M.S., Love J.A., and Grubbs R.H. J. Am. Chem. Soc. 123 (2001) 6543-6554
49. Love J.A., Morgan J.P., Trnka T.M., and Grubbs R.H. Angew. Chem., Int. Ed. 41 (2002) 4035-4037
50. Love J.A., Sanford M.S., Day M.W., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 10103-10109