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

Abstract : 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.
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https://hal.archives-ouvertes.fr/hal-01687211
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Submitted on : Thursday, January 18, 2018 - 11:41:22 AM
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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. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2017, 359 (20), pp.3638-3641. ⟨10.1002/adsc.201700735⟩. ⟨hal-01687211⟩

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