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Zhi-Shi Ye, Mu-Wang Chen, Qing-An Chen, Lei Shi, Ying Duan and Prof. Yong-Gui Zhou Iridium-Catalyzed Asymmetric Hydrogenation of Pyridinium Salts Angewandte Chemie International Edition 51

Version of Record online: 11 SEP 2012 | DOI: 10.1002/anie.201205187

Thumbnail image of graphical abstract

Highly efficient iridium-catalyzed asymmetric hydrogenations of simple 2-substituted pyridinium salts gives the chiral 2-substituted piperidines with up to 93 % ee (see picture; cod=1,5-cyclooctadiene; synphos=(5,6),(5′,6′)-bis(ethylenedioxy)-2,2′-bis(diphenylphosphino)-1,1′-biphenyl). The key feature of this strategy is the activation of simple pyridines as the pyridinium salts, thus eliminating substrate inhibition and enhancing the reactivity.

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