Short and Straightforward Enantioselective Synthesis of Both Enantiomers of Mequitazine through Iridium-Catalyzed Asymmetric Hydrogenation of a Nonfunctionalized Cyclic Enamine - Université de Rennes Accéder directement au contenu
Article Dans Une Revue SYNLETT Année : 2014

Short and Straightforward Enantioselective Synthesis of Both Enantiomers of Mequitazine through Iridium-Catalyzed Asymmetric Hydrogenation of a Nonfunctionalized Cyclic Enamine

Larquetoux Laurent
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Maillos Philippe
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Marc Nicolas
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Résumé

A short and straightforward asymmetric synthesis of both enantiomers of the antihistaminic drug mequitazine is reported. This atom-economical and attractive method features an iridium-catalyzed asymmetric hydrogenation of a nonfunctionalized cyclic enamine as a key step to install the C 3-stereogenic center. After a full investigation of the effects of catalyst precursors, ligands, solvents, temperature, and hydrogen pressure, mequitazine (1) is obtained in good yield (up to 80%) and with acceptable enantiomeric excesses up to 47%.

Domaines

Chimie
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Dates et versions

hal-01120064 , version 1 (24-02-2015)

Identifiants

Citer

Sébastien Gauthier, Larquetoux Laurent, Maillos Philippe, Tahar Ayad, Marc Nicolas, et al.. Short and Straightforward Enantioselective Synthesis of Both Enantiomers of Mequitazine through Iridium-Catalyzed Asymmetric Hydrogenation of a Nonfunctionalized Cyclic Enamine. SYNLETT, 2014, 25 (11), pp.1606-1610. ⟨10.1055/s-0033-1341274⟩. ⟨hal-01120064⟩
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