Perruthenate ion. Another metal oxo species able to promote the oxidative cyclisation of 1,5-dienes to 2,5-disubstituted cis-tetrahydrofurans

Tetrahedron Letters

Volumn 45, Issue 2, 2004, Pages 303-308

  Piccialli, Vincenzo ^a   Caserta, Teresa ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

1,5 Dienes; cis Tetrahydrofurans; NMO; Oxidative cyclisation; RuO4 ; TBAPI; TPAP

Indexed keywords

AMMONIUM DERIVATIVE; ION; TETRAHYDROFURAN DERIVATIVE; TETRAPROPYLAMMONIUM PERRUTHENATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0346366638     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.173     Document Type: Article

References (28)

1. 4: Charlsen P.H.J., Katsuki T., Martin V.S., Sharpless K.B. J. Org. Chem. 46:1981;3936-3938
2. Piccialli V., Cavallo N. Tetrahedron Lett. 42:2001;4695-4699.
3. 4: de Champdoré M., Lasalvia M., Piccialli V. Tetrahedron Lett. 39:1998;9781-9784
4. Donohoe T.J., Winter J.J.G., Helliwell M., Stemp G. Tetrahedron Lett. 42:2001;971-974
5. Donohoe T.J., Butterworth S. Angew. Chem., Int. Ed. 42:2003;948-951.
6. -: Klein E., Rojahn W. Tetrahedron. 21:1965;2353-2358
7. (g) Baldwin J.E., Crossley M.J., Lehtonen E.-M.M. J. Chem. Soc., Chem. Commun. 1979;918-919
8. (h) Walba D.M., Wand M.D., Wilkes M.C. J. Am. Chem. Soc. 101:1979;4396-4397
9. (i) Walba D.M., Edwards P.D. Tetrahedron Lett. 21:1980;3531-3534
10. (j) Spino C., Weiler L. Tetrahedron Lett. 28:1987;731-734
11. (k) Walba D.M., Przybyla C.A., Walker C.B.J. J. Am. Chem. Soc. 112:1990;5624-5625
12. Kocienskyi P.J., Brown R.C.D., Pommier A., Procter M., Schmidt B. J. Chem. Soc., Perkin Trans. 1998;9-39
13. Brown R.C.D., Hughes R.M., Keily J., Kenney A. Chem. Commun. 2000;1735-1736
14. Brown R.C.D., Keily J.F. Angew. Chem., Int. Ed. 40:2001;4496-4498.
15. For related oxidative monocyclisations of 5,6-dihydroxyalkenes, see; Walba D.M., Stoudt G.S. Tetrahedron Lett. 23:1982;727-730.
16. (a) Zeng L., Oberlies N.H., Shi G., Gu Z.-M., He K., McLaughlin J.L. Nat. Prod. Rep. 1996;275-306
17. (b) Alali F.Q., Liu X.X., McLaughlin J.L. J. Nat. Prod. 62:1999;505-540.
18. (a) See Refs. [1b,1c] and Piccialli V. Tetrahedron Lett. 41:2000;3731-3733
19. (b) Bifulco G., Caserta T., Gomez-Paloma L., Piccialli V. Tetrahedron Lett. 43:2002;9265-9269. corrigendum Tetrahedron Lett. 2003, 44, 3429
20. (c) Bifulco G., Caserta T., Gomez-Paloma L., Piccialli V. Tetrahedron Lett. 44:2003;5499-5503.
21. Ley S.V., Norman J., Griffith W.P., Marsden S.P. Synthesis. 1994;639-666.
22. 1f.
23. 2/AcOH was ca. 30 mg/mL. The use of molecular sieves appears not to affect appreciably both processes but their presence facilitates the work-up.
24. See, for example, the synthesis of related D-chitaric acid reported in Ref. [1e].
25. After a prolonged treatment a<5 % of (E)-tetradec-6-en-5-one was obtained.
26. (a) Lee D.G., Chang V.S., Helliwell S. J. Org. Chem. 41:1976;3644-3646
27. (b) Lee D.G., Helliwell S. Can. J. Chem. 62:1984;1085-1092.
28. Travis B., Borhan B. Tetrahedron Lett. 42:2001;7741-7745. and references cited therein.