Diradical-promoted (n + 2 - 1) ring expansion: An efficient reaction for the synthesis of macrocyclic ketones

Organic Letters

Volumn 6, Issue 18, 2004, Pages 3179-3181

  Rüedi, Georg ^a   Oberli, Matthias A ^a   Nagel, Matthias ^a,b   Hansen, Hans Jurgen ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANONE; KETONE DERIVATIVE; MACROCYCLIC COMPOUND; METHYL GROUP; VINYL DERIVATIVE;

ARTICLE; CARBONYLATION; CHEMICAL MODIFICATION; PYROLYSIS; VACUUM;

EID: 4544361138     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048701e     Document Type: Article

References (30)

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16. In a recent paper, we provided evidence that vinyl insertion occurs via open-chain diradical intermediate states, rather than via formally disallowed 1,3-sigmatropoic shifts; see: Rüedi, G.; Hansen, H.-J. Helv. Chim. Acta 2004, 87, 1628.
17. In connection with this study, we have developed a practical and user-friendly method for the selenium-free one-step preparation of 1,2-diketones by treating the corresponding cycloalkanones with sodium nitrite and HCl in THF at low temperatures.
18. 1H NMR showed a low field shifted singlet at 4.19 ppm accounting for a OH group being part of a hydrogen bridge.
19. As a control experiment 1,2-dione 9 was subjected to FVP at 600 °C to give 7 (67%), doubly decarbonylated cyclododecane (16%), and unreacted starting material (10%). In contrast, 9 remained unaffected when treated at temperatures below 540°C.
20. The lower overall yield may be attributed to double decarbonylation and dehydration.
21. The initially formed silylenol ether compounds were each obtained as 1:1 mixture of E/Z-isomers.
22. Lower temperatures gave rise to incomplete conversion.
23. Compounds 10d-h were prepared in good yields by addition of the corresponding 1-alkenylmagnesium bromide reagent to the appropriate 1,2-diketone, followed by silylation.
24. For recent reviews on macrocyclic musks, see: (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633. (b) Williams, A. S. Synthesis 1999, 1707. (c) Fráter, G.; Bajgrowicz, J. A.; Denis, C.; Kraft, P. Angew. Chem., Int. Ed. 2000, 39, 2980.
25. For recent reviews on macrocyclic musks, see: (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633. (b) Williams, A. S. Synthesis 1999, 1707. (c) Fráter, G.; Bajgrowicz, J. A.; Denis, C.; Kraft, P. Angew. Chem., Int. Ed. 2000, 39, 2980.
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27. Precursor 10e was obtained on a multigram scale from low-priced cyclododecanone through a five-step synthesis in ca. 60% overall yield. For details, see refs 4a,b and 6.
28. Recent examples: (a) Rüedi, G.; Nagel, M.; Hansen, H.-J. Org. Lett. 2003, 5, 2691. (b) Rüedi, G.; Nagel, M.; Hansen, H.-J. Org. Lett. 2003, 5, 4211. (c) Rüedi, G.; Nagel, M.; Hansen, H.-J. Synlett 2003, 1210.
29. Recent examples: (a) Rüedi, G.; Nagel, M.; Hansen, H.-J. Org. Lett. 2003, 5, 2691. (b) Rüedi, G.; Nagel, M.; Hansen, H.-J. Org. Lett. 2003, 5, 4211. (c) Rüedi, G.; Nagel, M.; Hansen, H.-J. Synlett 2003, 1210.
30. Recent examples: (a) Rüedi, G.; Nagel, M.; Hansen, H.-J. Org. Lett. 2003, 5, 2691. (b) Rüedi, G.; Nagel, M.; Hansen, H.-J. Org. Lett. 2003, 5, 4211. (c) Rüedi, G.; Nagel, M.; Hansen, H.-J. Synlett 2003, 1210.