Highly Enantioselective Arylation of N-Tosylalkylaldimines Catalyzed by Rhodium-Diene Complexes

Zhe Cui, Hong-Jie Yu, Rui-Feng Yang, Wen-Yun Gao, Chen-Guo Feng* and Guo-Qiang Lin*

*Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P.R. China, Email: fengcgsioc.ac.cn; lingqmail.sioc.ac.cn

Z. Cui, H.-J. Yu, F.-F. Yang, W.-Y. Gao, C.-G. Feng, G.-Q. Lin, J. Am. Chem. Soc., 2011, 133, 12394-12397.

DOI: 10.1021/ja2046217

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Abstract

The combination of chiral bicyclo[3.3.0]octadiene ligands, an active rhodium hydroxide complex, and neutral reaction conditions enabled a highly enantioselective rhodium-catalyzed arylation of aliphatic N-tosylaldimines in high yield. The application of this method is demonstrated by the enantioselective synthesis of chiral 2-aryl pyrrolidines and piperidines in a one-pot procedure.

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Key Words

Arylation, Pyrrolidines, Piperidines

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ID: J48-Y2011-2230