Asymmetric Intramolecular Oxa-Michael Reactions of Cyclohexadienones Catalyzed by a Primary Amine Salt

Authors

  • Wenbin Wu,

    1. Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China)
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  • Xin Li,

    1. Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China)
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  • Huicai Huang,

    1. Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China)
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  • Xiaoqian Yuan,

    1. Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China)
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  • Junzhu Lu,

    1. Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China)
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  • Kailong Zhu,

    1. Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China)
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  • Prof. Dr. Jinxing Ye

    Corresponding author
    1. Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China)
    • Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China)
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  • This work was supported by the Innovation Program of Shanghai Municipal Education Commission (11ZZ56), the National Natural Science Foundation of China (21272068), the Fundamental Research Funds for the Central Universities, and the Shanghai Committee of Science and Technology (11DZ2260600).

Abstract

original image

Michael brings the rings: An asymmetric intramolecular oxa-Michael reaction involving iminium activation has been developed. This reaction provides enantioenriched 1,4-dioxane derivatives with up to 99 % yield and 98 % ee. The method allows for concise and stereoselective access to stereodiverse, complex tetracyclic compounds containing a bicyclo[2.2.2]octan-2-one backbone with multiple chiral centers.

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