Exploring the metal-catalyzed reaction of furans with alkyl α-diazomethanesulfonate and α-diazomethanephosphonate: synthesis of ω-acyl-substituted sulfono- and phosphonobutadienes

Tetrahedron

Volumn 65, Issue 34, 2009, Pages 7092-7098

  Marinozzi, Maura ^a   Fulco, Maria Carmela ^a   Amori, Laura ^a   Fiumi, Massimiliana ^a   Pellicciari, Roberto ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHOXYFURAN; 2 METHYLFURAN; ALKADIENE; ALKYL GROUP; ALPHA DIAZOMETHANEPHOSPHONIC ACID; ALPHA DIAZOMETHANESULFONIC ACID; CYCLOPROPANE DERIVATIVE; DICHLOROMETHANE; FURAN DERIVATIVE; METAL; PHOSPHONIC ACID DERIVATIVE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 67650523210     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.040     Document Type: Article

References (33)

1. Wenkert E., Guo M., Lavilla R., Porter B., Ramachandran K., and Sheu J.-H. J. Org. Chem. 55 (1990) 6203-6214 and references cited therein
2. Matlin S.A., Chan L., and Catherwood B. J. Chem. Soc., Perkin Trans. 1 (1990) 89-96
3. Wenkert E., and Khatuya H. Helv. Chim. Acta 82 (1999) 511-514
4. Wenkert E., and Khatuya H. Tetrahedron Lett. 40 (1999) 5439-5442
5. Shieh P.C., and Ong C. Tetrahedron 57 (2001) 7303-7307
6. Müller P., Allenbach Y.F., and Bernardinelli G. Helv. Chim. Acta 86 (2003) 3164-3178
7. Schinnerl M., Böhm C., Seitz M., and Reiser O. Tetrahedron: Asymmetry 14 (2003) 765-771
8. Hahn N.D., Nieger M., and Dötz K.H. J. Organomet. Chem. 689 (2004) 2662-2673
9. Hedley S.J., Ventura D.L., Dominiak P.M., Nygren C.L., and Davies H.M.L. J. Org. Chem. 71 (2006) 5349-5356
10. Doyle M.P., McKervey M.A., and Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds (1998), John Wiley & Sons, New York, NY see Chapter 6.4, pp 73-78
11. Böhm C., and Reiser O. Org. Lett. 3 (2001) 1315-1318
12. Monn J.A., Valli M.J., Massey S.M., Hansen M.M., Kress T.J., Wepsiec J.P., Harkness A.R., Grutsch J.L., Wright R.A., Johnson B.G., Andis S.L., Kingston A., Tomlinson R., Lewis R., Griffey K.R., Tizzano J.P., and Schoepp D.D. J. Med. Chem. 42 (1999) 1027-1040
13. Padwa A., Wisnieff T.J., and Walsh E.J. J. Org. Chem. 51 (1986) 5036-5038
14. Wenkert E., Guo M., Pizzo F., and Ramachandran K. Helv. Chim. Acta 70 (1987) 1429-1438
15. Padwa A., Wisnieff T.J., and Walsh E.J. J. Org. Chem. 54 (1989) 299-308
16. Davies H.M.L., and Calvo R.L. Tetrahedron Lett. 38 (1997) 5623-5626
17. Doyle M.P., Chapman B.J., Hu W., Peterson C.S., McKervey M.A., and Garcia C.F. Org. Lett. 1 (1999) 1327-1329
18. Curini M., Epifano F., Marcotullio M.C., Rosati O., Guo M., Guan Y., and Wenkert E. Helv. Chim. Acta 88 (2005) 330-338
19. Hughes C.C., Kennedy-Smith J.J., and Trauner D. Org. Lett. 5 (2003) 4113-4115
20. Berkessel A., and Voges M. Chem. Ber. 122 (1989) 1147-1151
21. Ye T., and Zhou C. New J. Chem. 29 (2005) 1159-1163
22. Pellicciari R., Marinozzi M., Macchiarulo A., Fulco M.C., Gafarova J., Serpi M., Giorgi G., Nielsen S., and Thomsen C. J. Med. Chem. 50 (2007) 4630-4641
23. Seyferth D., Marmor R.S., and Hilbert P. J. Org. Chem. 6 (1971) 1379-1386
24. Regitz M. Angew. Chem., Int. Ed. Engl. 14 (1975) 222-231
25. Bäckvall J.-E., Chinchilla R., Nájera C., and Yus M. Chem. Rev. 98 (1998) 2291-2312
26. Takao K., Munakata R., and Tadano K. Chem. Rev. 105 (2005) 4779-4807
27. Reymond S., and Cossy J. Chem. Rev. 108 (2008) 5359-5406
28. Rokach J., Guindon Y., Young R.N., Adams J., and Atkinson J.G. In: ApSimon J. (Ed). The Total Synthesis of Natural Products Vol. 7 (1988), Wiley
29. Engel R. Chem. Rev. 77 (1977) 349-369
30. Palacios F., Alonso C., and de los Santos J.M. Chem. Rev. 105 (2005) 899-931
31. Griffiths R. Biochem. Soc. Trans. 21 (1993) 66-72
32. Angaw-Duguma L., Marecek J., and Seltzer S. Bioorg. Chem. 20 (1992) 213-222
33. Huang X., Zhang C., and Lu X. Synthesis (1995) 769-771