Cyclobutenes as isolable intermediates in the gold(I)-catalysed cycloisomerisation of 1,8-enynes

Abstract : The gold(I)-catalysed isomerisation of 1,8-enynes allows the efficient synthesis of function -alised bicyclo[5.2.0]nonenes. Notably, these cyclobutenes derivatives can be isolated as reactive intermediates that could undergo subsequent gold(I)-catalysed transformations such as isomerisation, fragmentation or ene reaction to furnish more structurally complex products. This study also provides useful information related to the mechanism leading to metathesis-type derivatives, examples of which were shown to be produced, in the present case, by a gold(I)-catalysed ring fragmentation of the cyclobutene moiety. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
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Yann Odabachian, Fabien Gagosz. Cyclobutenes as isolable intermediates in the gold(I)-catalysed cycloisomerisation of 1,8-enynes. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2009, 351 (3), pp.379-386. ⟨10.1002/adsc.200900056⟩. ⟨hal-00951266⟩

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