9 research outputs found

    Ethyl (3 S

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

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    International audienceA 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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