Hydroalkylation of alkynyl Ethers via a gold(I)-catalyzed 1,5-hydride shift/cyclization sequence

Igor Jurberg 1 Yann Odabachian 1 Fabien Gagosz 1, *
* Corresponding author
1 DCSO - Laboratoire de synthèse organique
Abstract : A series of alkynyl ethers react with an electrophilic gold(I) catalyst to produce a range of structurally complex spiro or fused dihydrofurans and dihydropyrans via a 1,5-hydride shift/cyclization sequence. This hydroalkylation process, which is performed under practical experimental conditions, can be applied to terminal as well as ester-substituted alkynes. It allows the efficient conversion of secondary or tertiary sp3 C-H bonds into new C-C bonds by the nucleophilic addition of a vinylgold species onto an oxonium intermediate. The stereoselectivity of the cycloisomerization process toward the formation of a new five- or six-membered cycle appears to be dependent on steric factors and the alkyne substitution pattern. © 2010 American Chemical Society.
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Submitted on : Friday, February 28, 2014 - 2:28:18 PM
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Igor Jurberg, Yann Odabachian, Fabien Gagosz. Hydroalkylation of alkynyl Ethers via a gold(I)-catalyzed 1,5-hydride shift/cyclization sequence. Journal of the American Chemical Society, American Chemical Society, 2010, 132 (10), pp.3543-3552. ⟨10.1021/ja9100134⟩. ⟨hal-00951253⟩

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