期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 31, 页码 9772-9778出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200801088
关键词
alkenes; catalysis; cycloaddition reactions; cyclohexadienes; diynes; ruthenium
资金
- M.E.C. (Spain)
- FEDER [CTQ2005-08613]
- Consolider Ingenio 2010 [CSD2007-00006]
- Xunta de Galicia [2007/XA084, PGIDIT06PXIC209041PN]
Fomal and standard Ru-II-catalyzed [2+2+21 cycloaddition of 1.6-diynes to alkenes gave bicyclic 1,3-cyclohexadienes in relatively good yields. When terminal 1,6-diynes 1 were used, two isomeric bicyclic 1,3-cyclohexadienes 4 or 6 were obtained, depending on the acyclic or cyclic nature of the alkene partner. When unsymmetrical substituted 1,6-diynes 7 were used, the reaction with acyclic alkenes took place regio- and stereoselectively to afford bicyclic 1,3-cyclohexadienes 8. A cascade process that behaves as a formal Ru-II-catalyzed [2+2+2] cyclo-addition explained these results. Initially a Ru-catalyzed linear coupling of 1,6-diynes 1 and 7 with acyclic alkenes occurs to give open 1,3,5-trienes of type 3, which after a thermal disrotatory 6e(-)pi-electrocyclization led to the final 1,3-cyclohexadienes 4 and 8. When disubstituted 1,6-diyne 10 was used with electron-deficient alkenes, new exo-methylene cyclohexadienes 12 arose from it competitive reaction path-way.
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