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Chiral Primary Amine Catalyzed α-Arylation of Simple Ketones via Asymmetric Retro-Claisen Cleavage |
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| Authors: | Yanfang Han Mingying Shi Dr Xueling Mi Prof?Dr Sanzhong Luo |
| Institution: | 1. Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (P. R. China) and, School of Chemical Science, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China;2. College of Chemistry, Beijing Normal University, Beijing, 100875 P. R. China;3. Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084 P. R. China |
| Abstract: | Highly enantioselective α-arylation of simple ketones has been achieved by chiral primary amine catalyzed asymmetric retro-Claisen cleavage of β-diketones. This mild organocatalytic strategy enables the construction of α-aryl tertiary carbon stereocenters in good yields and excellent enantioselectivities (up to 98 % ee) with the para-quinone monoimines as aryl sources. Furthermore, oxidative catalytic asymmetric α-arylation has also been realized with free p-aminophenols. |
| Keywords: | α-arylation β-diketone chiral primary amine quinone imine retro-Claisen cleavage |