Iridium-Catalyzed Asymmetric Hydrogenation of α-Substituted α,β-Unsaturated Acyclic Ketones: Enantioselective Total Synthesis of (-)-Mesembrine

Qian-Qian Zhang, Jian-Hua Xie*, Xiao-Hui Yang, Jian-Bo Xie and Qi-Lin Zhou*

*State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China, Email: jhxienankai.edu.cn, qlzhounankai.edu.cn

Q.-Q. Zhang, J.-H. Xie, X.-H. Yang, J.-B. Xie, Q.-L. Zhou, Org. Lett., 2012, 14, 6158-6161.

DOI: 10.1021/ol3030956

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Abstract

A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones in the presence of chiral spiro iridium complexes provides chiral 2-substituted allylic alcohols and a concise route to (-)-mesembrine.

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Key Words

Reduction of α,β-unsaturated compounds, hydrogen

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ID: J54-Y2012-3840