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Synthesis of Enantioenriched 2-Alkyl Piperidine Derivatives through Asymmetric Reduction of Pyridinium Salts.

ABSTRACT: 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.

SUBMITTER: Qu B

PROVIDER: S-EPMC10405300 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Synthesis of Enantioenriched 2-Alkyl Piperidine Derivatives through Asymmetric Reduction of Pyridinium Salts.

Qu Bo B Mangunuru Hari P R HP Wei Xudong X Fandrick Keith R KR Desrosiers Jean-Nicolas JN Sieber Joshua D JD Kurouski Dmitry D Haddad Nizar N Samankumara Lalith P LP Lee Heewon H Savoie Jolaine J Ma Shengli S Grinberg Nelu N Sarvestani Max M Yee Nathan K NK Song Jinhua J JJ Senanayake Chris H CH

Organic letters 20160923 19

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. ...[more]

PMID: 27661252

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