The role of cyclobutenes in gold(I)-catalysed skeletal rearrangement of 1,6-enynes |
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Authors: | Escribano-Cuesta Ana Pérez-Galán Patricia Herrero-Gómez Elena Sekine Masaki Braga Ataualpa A C Maseras Feliu Echavarren Antonio M |
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Institution: | Institute of Chemical Research of Catalonia (ICIQ), Av. Pa?sos Catalans 16, 43007 Tarragona, Spain. |
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Abstract: | 1,6-Enynes with electron-donating substituents at the alkyne undergo gold(I)-catalysed single cleavage skeletal rearrangement, whereas substrates with electron-withdrawing substituents evolve selectively to double cleavage rearrangement. Theoretical calculations provide a qualitative rationale for these effects, and suggest that bicyclo3.2.0]hept-5-enes are involved as intermediates. We provide the first X-ray structural evidence for the formation of a product of this class in a cycloisomerisation of a 1,6-enyne. |
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