Expeditious Synthesis of Enantioenriched Tetrahydropyrans via Chemoselective C−N bond Cleavage of Aza-Oxa-Bicyclo[3.2.1]Octanes
| Autor: | Damien Bonne, Jean Rodriguez, Sébastien Goudedranche, Thierry Constantieux, Cecilia Sasso D'Elia, Marco Bella |
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| Přispěvatelé: | Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC), Dipartimento di Chimica, Università degli Studi di Roma 'La Sapienza' = Sapienza University [Rome], Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Università degli Studi di Roma 'La Sapienza' = Sapienza University [Rome] (UNIROMA) |
| Rok vydání: | 2017 |
| Předmět: |
Bicyclic molecule
Organocatalysis Oxocarbenium ions [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Chemistry Oxocarbenium Azepanes Multiple bond-forming transformations Tetrahydropyrans Organo- catalysis General Chemistry Tetrahydropyran 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Electrophile Enantiomeric excess Bond cleavage Octane |
| Zdroj: | Advanced Synthesis and Catalysis Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2017, 359 (20), pp.3638-3641. ⟨10.1002/adsc.201700735⟩ Advanced Synthesis and Catalysis, 2017, 359 (20), pp.3638-3641. ⟨10.1002/adsc.201700735⟩ |
| ISSN: | 1615-4150 1615-4169 |
| DOI: | 10.1002/adsc.201700735 |
| Popis: | International audience; 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. |
| Databáze: | OpenAIRE |
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