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Highly Enantioselective [3+3] Cycloaddition of Aromatic Azomethine Imines with Cyclopropanes Directed by π–π Stacking Interactions

Authors

  • You-Yun Zhou,

    1. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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    • These authors contributed equally to this work.

  • Jun Li,

    1. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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    • These authors contributed equally to this work.

  • Lin Ling,

    1. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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    • L. Ling conducted the calculation.

  • Dr. Sai-Hu Liao,

    1. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • Dr. Xiu-Li Sun,

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai 200032 (P.R. China)
    • State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • Prof. Dr. Yu-Xue Li,

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai 200032 (P.R. China)
    • State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • Dr. Li-Jia Wang,

    1. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • Prof. Dr. Yong Tang

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai 200032 (P.R. China)
    • State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • We are grateful for the financial support from the National Natural Sciences Foundation of China (nos. 20932008, 21072207, and 21121062), the Major State Basic Research Development Program (grant no. 2009CB825300), and the Chinese Academy of Sciences.

Abstract

original image

Designing armory: The side-arm-modified In-TOX/NiII complex was identified as a highly efficient and stereoselective catalyst for the [3+3] cycloaddition of aromatic azomethine imines with cyclopropanes (see picture). Density functional calculations and control experiments revealed that the directing effect of the side arm through π interactions is crucial to the stereochemical control.

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