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Aromatic Spiroketal Bisphosphine Ligands: Palladium-Catalyzed Asymmetric Allylic Amination of Racemic Morita–Baylis–Hillman Adducts

Authors

  • Xiaoming Wang,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P. R. China)
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  • Fanye Meng,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P. R. China)
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  • Yan Wang,

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
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  • Dr. Zhaobin Han,

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

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
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  • Prof. Dr. Li Liu,

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
    • Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
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  • Dr. Zheng Wang,

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P. R. China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P. R. China)
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  • Prof. Dr. Kuiling Ding

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P. R. China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P. R. China)
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  • We thank the NSFC (grant nos. 21172237, 21121062, 21032007), Major Basic Research Development Program of China (grant no. 2010CB833300), and the Chinese Academy of Sciences for financial support of this work.

Abstract

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Showing a backbone: The spiroketal backbone of the bis(phosphine) ligand 1 led to good regio- and enantioselectivity in the palladium-catalyzed asymmetric allylic amination of racemic Morita–Baylis–Hillman adducts with aromatic amines. The methodology provides a facile and efficient synthesis of precursors for optically active β-lactam derivatives, including the cholesterol drug Ezetimibe.

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