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Enantioselective Aza-Henry Reaction of Imines Bearing a Benzothiazole Moiety Catalyzed by a Cinchona-Based Squaramide

Authors

  • Hai-Xiao He,

    1. School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China, Fax: (+86)-010-6891-4985
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  • Wen Yang,

    1. School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China, Fax: (+86)-010-6891-4985
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  • Da-Ming Du

    Corresponding author
    1. School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China, Fax: (+86)-010-6891-4985
    • School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China, Fax: (+86)-010-6891-4985
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Abstract

An efficient enantioselective aza-Henry reaction of nitroalkanes to imines bearing a benzothiazole moiety catalyzed by a Cinchona-based squaramide has been developed. In the reaction of imines, the corresponding products were obtained in good to excellent yields (up to 99%) with excellent enantioselectivities (up to >99% ee) for most of the aromatic substituted imines. The imines with electron-withdrawing groups gave better yields than those bearing electron-donating groups in the aza-Henry reaction. Moreover, a one-pot three-component enantioselective aza-Henry reaction using 2-aminobenzothiazoles, aldehydes, and nitromethane was also developed. Moderate to good yields and high enantioselectivities were obtained in the one-pot cases (up to 98% ee).

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