Regioselective Michael-induced cyclisation of γ- and δ-hydroxy vinyl sulfides and vinyl dithiocarbamates

Abstract : We herein describe the unprecedented use of heteroaryl vinyl sulfides and vinyl dithiocarbamates as hetero-Michael addition acceptors. Combined chelating and electron-withdrawing effects are postulated to stabilise the transient anionic species and allow smooth Michael-induced ring closure to produce diversely functionalised C-glycosides.
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https://hal.archives-ouvertes.fr/hal-02086017
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Submitted on : Monday, April 1, 2019 - 9:51:03 AM
Last modification on : Thursday, April 4, 2019 - 1:36:56 AM

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V. Aucagne, C. Lorin, A. Tatibouët, P. Rollin. Regioselective Michael-induced cyclisation of γ- and δ-hydroxy vinyl sulfides and vinyl dithiocarbamates. Tetrahedron Letters, Elsevier, 2005, 46 (25), pp.4349-4352. ⟨10.1016/j.tetlet.2005.04.112⟩. ⟨hal-02086017⟩

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