Expeditious Synthesis of Enantioenriched Tetrahydropyrans via Chemoselective C N bond Cleavage of Aza-Oxa-Bicyclo[3.2.1] Octanes - MédiHAL Accéder directement au contenu
Image (Illustration) Année : 2017

Expeditious Synthesis of Enantioenriched Tetrahydropyrans via Chemoselective C N bond Cleavage of Aza-Oxa-Bicyclo[3.2.1] Octanes

Résumé

A rapid synthesis of enantioenriched 2,3,4-trisubstituted tetrahydropyrans in good yields and stereoselectivities is reported. The first step is a domino organocatalytic reaction between ambident electrophilic and 1,4-bis-nucleophilic 1,2-ketoamides and 1,3-bis-electrophilic enals, leading to aza-oxa-bicyclo[3.2.1]octane. Then, the TiCl4/Et3SiH system ensures a chemoselective cleavage of the C−N bond and affords the desired trisubstituted tetrahydropyran in good yield and with conservation of the precursors optical purity. This final synthetic operation includes two consecutive oxocarbenium ion formation and reductions.

Domaines

Chimie organique

Dates et versions

medihal-01723176 , version 1 (05-03-2018)

Licence

Domaine public

Identifiants

  • HAL Id : medihal-01723176 , version 1

Citer

Cecilia Sasso d'Elia, Sébastien Goudedranche, Thierry Constantieux, Marco Bella, Damien Bonne, et al.. Expeditious Synthesis of Enantioenriched Tetrahydropyrans via Chemoselective C N bond Cleavage of Aza-Oxa-Bicyclo[3.2.1] Octanes. Illustration. France. 2017. ⟨medihal-01723176⟩
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