Catalytic cyclization of alkenyl N,O-acetals by Fe(OTf) 3

Chemistry Letters

Volumn 38, Issue 7, 2009, Pages 724-725

  Komeyama, Kimihiro ^a   Igawa, Ryoichi ^a   Morimoto, Takayuki ^a   Takaki, Ken ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67650481812     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.724     Document Type: Article

References (14)

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3. Ring-closing metathesis (RCM) of nitrogen tethered α, ω-dienes:
4. A. Deiters, S. F. Martin, Chem. Rev. 2004, 104, 2199.
5. a) J. Royer, M. Bonin, L. Micouin, Chem. Rev. 2004, 104, 2311.
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7. Solvent effect in Entry 8 (Table I) : 1, 4-dioxane (73%, 3 h) ; 1, 2-dichloroethane (67%, 7 h) ; 1, 2-dimethoxyethane (52%, 3 h) ; toluene (42%, 48 h).
8. 2. After completion of the reaction, the resulting mixture was passed through a short silica gel column with ether eluent, and then concentrated. The crude product was purified by column chromatography on silica gel with EtOAc-hexane (50/50) eluent to afford the azacycloalkene 2.
9. 13C NMR, and GC-MS. However, it was difficult to determine the exact position of the olefinic moiety, because they were not separable. A similar situation was encountered in other heterocycles 2c-2h.
10. 10
11. H. Hiemstra, W. N. Speckamp, in Comprehensive Organic Synthesis, ed. by B. M. Trost, I. Fleming, Pergamon Press, Oxford, 1991, Vol. 2, p. 1047.
12. 1H NMR data for olefinic resonances of cationic gold (I) π-alkene complexes and free alkenes. T. J. Brown, M. G. Dickens, R. A. Widenhoefer, J. Am. Chem. Soc. 2009, ASAP.
13. K. Komeyama, K. Takahashi, K. Takaki, Org. Lett. 2008, 10, 5119.
14. Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.