Synthesis of Enantioenriched 2-Alkyl Piperidine Derivatives through Asymmetric Reduction of Pyridinium Salts.
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An Ir-catalyzed enantioselective hydrogenation of 2-alkyl-pyridines has been developed using ligand MeO-BoQPhos. High levels of enantioselectivities up to 93:7 er were obtained. The resulting enantioenriched piperidines can be readily converted into biologically interesting molecules such as the fused tricyclic structures 5, 6, and 7 in 99:1 er, providing a novel, concise synthetic route to this family of chiral piperidine-containing compounds.
author list (cited authors)
Qu, B. o., Mangunuru, H., Wei, X., Fandrick, K. R., Desrosiers, J., Sieber, J. D., ... Senanayake, C. H.
complete list of authors
Qu, Bo||Mangunuru, Hari PR||Wei, Xudong||Fandrick, Keith R||Desrosiers, Jean-Nicolas||Sieber, Joshua D||Kurouski, Dmitry||Haddad, Nizar||Samankumara, Lalith P||Lee, Heewon||Savoie, Jolaine||Ma, Shengli||Grinberg, Nelu||Sarvestani, Max||Yee, Nathan K||Song, Jinhua J||Senanayake, Chris H