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. (Figure presented.). © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Expeditious Synthesis of Enantioenriched Tetrahydropyrans via Chemoselective C−N bond Cleavage of Aza-Oxa-Bicyclo[3.2.1]Octanes / Sasso D'Elia, Cecilia; Goudedranche, Sébastien; Constantieux, Thierry; Bella, Marco; Bonne, Damien; Rodriguez, Jean. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 359:20(2017), pp. 3638-3641. [10.1002/adsc.201700735]

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

Sasso D'Elia, Cecilia;Bella, Marco
;
2017

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. (Figure presented.). © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
2017
Azepanes; Multiple bond-forming transformations; Organocatalysis; Oxocarbenium ions; Tetrahydropyrans
01 Pubblicazione su rivista::01a Articolo in rivista
Expeditious Synthesis of Enantioenriched Tetrahydropyrans via Chemoselective C−N bond Cleavage of Aza-Oxa-Bicyclo[3.2.1]Octanes / Sasso D'Elia, Cecilia; Goudedranche, Sébastien; Constantieux, Thierry; Bella, Marco; Bonne, Damien; Rodriguez, Jean. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 359:20(2017), pp. 3638-3641. [10.1002/adsc.201700735]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1514371
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