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Asymmetric Synthesis of Wieland-Miescher and Hajos-Parrish Ketones Catalyzed by an Amino-Acid-Derived Chiral Primary Amine

Pengxin Zhou, Long Zhang, Sanzhong Luo* and Jin-Pei Cheng

*Beijing National Laboratory for Molecule Sciences (BNLMS), Institute of Chemistry, the Chinese Academy of Sciences, Beijing, 100190 China, Email: luosziccas.ac.cn

P. Zhou, L. Zhang, S. Luo, J.-P. Cheng, J. Org. Chem., 2012, 77, 2526-2530.

DOI: 10.1021/jo202433v (free Supporting Information)


Abstract

A simple chiral primary amine catalyses a highly efficient reaction for the synthesis of both Wieland-Miescher ketone and Hajos-Parrish ketone as well as their analogues in high enantioselectivity and excellent yields. This procedure represents one of the most efficient methods for the synthesis of these versatile chiral building blocks even in gram scale with 1 mol% catalyst loading.

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Key Words

Cyclopentanones, Cyclohexanones, Cyclohexenones, Organocatalysis, Green Chemistry, Robinson Annulation


ID: J42-Y2012-0650