Skip to Main content Skip to Navigation
Journal articles

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

Abstract : 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%.
Document type :
Journal articles
Complete list of metadatas

https://hal-univ-rennes1.archives-ouvertes.fr/hal-01120064
Contributor : Béatrice Mahi <>
Submitted on : Tuesday, February 24, 2015 - 5:08:28 PM
Last modification on : Tuesday, September 22, 2020 - 3:37:45 AM

Identifiers

Citation

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, Georg Thieme Verlag, 2014, 25 (11), pp.1606-1610. ⟨10.1055/s-0033-1341274⟩. ⟨hal-01120064⟩

Share

Metrics

Record views

298