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Synfacts 2011(7): 0761-0761  
DOI: 10.1055/s-0030-1260659
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Piperidine Synthesis via Pd-Catalyzed Diastereoselective Cross-Coupling

Contributor(s): Hisashi Yamamoto, Zhi Li
S. Seel, T. Thaler, K. Takatsu, C. Zhang, H. Zipse, B. F. Straub, P. Mayer, P. Knochel*
Kyoto University, Japan; Ludwig-Maximilians-Universität München and Universität Heidelberg, Germany
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Publication History

Publication Date:
17 June 2011 (online)

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Significance

In this report, highly diastereo­selective syntheses of both cis- and trans-2,4-­disubstituted piperidines are described. The method is based on palladium-catalyzed Negishi coupling between substituted piperidinylzinc reagents and aryl iodides. Coupling with 4-substituted piperidin-2-ylzinc reagents provides cis-2,4-disubstituted products, while coupling with 2-substituted ­piperidin-4-ylzinc reagents provides the trans products.