Asymmetric Michael Addition of Aldimino Esters with Chalcones Catalyzed by Silver/Xing‐Phos: Mechanism‐Oriented Divergent Synthesis of Chiral Pyrrolines |
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| Authors: | Xing‐Feng Bai Dr Li Li Dr Zheng Xu Dr Zhan‐Jiang Zheng Prof?Dr Chun‐Gu Xia Dr Yu‐Ming Cui Prof?Dr Li‐Wen Xu |
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| Institution: | 1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics (CAS) and, University of the Chinese Academy of Sciences, P. R. China;2. Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, P. R. China |
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| Abstract: | The mechanism‐oriented reaction design for the divergent synthesis of chiral molecules from simple starting materials is highly desirable. In this work, aromatic amide‐derived nonbiarylatropisomer/silver (silver/Xing‐Phos) complex was used to catalyze the Michael addition of glycine aldimino esters to chalcones and successfully applied to the subsequent cyclocondensation to afford substituted cis‐Δ(1)‐pyrroline derivatives with up to 98 % ee. Besides the inherent performance of the chiral Ag/Xing‐Phos catalyst system, it was found that the workup of such reactions played an important role for the stereoselective construction of stereodivergent Δ(1)‐pyrrolines, in which an epimerization of the cis‐Δ(1)‐pyrrolines to the trans‐isomers during was revealed. |
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| Keywords: | asymmetric catalysis Michael reaction pyrrolines silver stereodivergent synthesis |
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