Asymmetric Binary Acid Catalysis: A Regioselectivity Switch between Enantioselective 1,2- and 1,4-Addition through Different Counteranions of InIII

Authors

  • Jian Lv,

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China), Fax: (+86) 10-6255-4449
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  • Dr. Long Zhang,

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China), Fax: (+86) 10-6255-4449
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  • Yueming Zhou,

    1. BNLMS, CAS Key Laboratory of Analytical Chemistry for Living Biosystems, Beijing 100190 (China)
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  • Prof. Zongxiu Nie,

    1. BNLMS, CAS Key Laboratory of Analytical Chemistry for Living Biosystems, Beijing 100190 (China)
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  • Prof. Sanzhong Luo,

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China), Fax: (+86) 10-6255-4449
    • Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China), Fax: (+86) 10-6255-4449
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  • Prof. Jin-Pei Cheng

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China), Fax: (+86) 10-6255-4449
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  • The project was supported by the Natural Science Foundation (NSFC; 20972163 and 21025208) and MOST (2011CB808600). J.L. thanks the China Postdoctoral Science Foundation for support.

Abstract

original image

You can count on the anion: Simply swapping the anions of an indium Lewis acid leads to a remarkable regioselectivity switch between asymmetric 1,2- and 1,4-addition reactions. N-protected indoles and β,γ-unsaturated α-keto esters gave adducts with excellent enantioselectivity (see scheme).

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