A General Approach to Various Five- and Six-Membered gem-Difluoroheterocycles Application to the Synthesis of Fluorinated Analogues of Sedamine

Abstract : A new synthesis of a group of O-, S- and N-heterocycles with a gem-difluoro group in position to the heteroatom has been developed, starting from easily accessible gem-difluoro propargylic derivatives. This tandem process involves a base-induced isomerization followed by an intramolecular 1,4 hetero-Michael addition. This methodology is suitable for the preparation of five- and six-membered heterocycles and it has been successfully applied to the synthesis of the 3,3-difluoro analogues of (+/-)-sedamine III, (+/-)-allosedamine V, (+/-)-norallosedamine II, and (+/-)-norsedamine IV.
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Submitted on : Friday, August 24, 2018 - 2:30:19 PM
Last modification on : Sunday, December 23, 2018 - 7:11:53 PM

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Layal Hariss, Rima Ibrahim, Nada Jaber, Thierry Roisnel, René Grée, et al.. A General Approach to Various Five- and Six-Membered gem-Difluoroheterocycles Application to the Synthesis of Fluorinated Analogues of Sedamine. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2018, pp.3782-3791. ⟨10.1002/ejoc.201800371⟩. ⟨hal-01861423⟩

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