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Enantioselective Synthesis of AG-041R by using N-Heteroarenesulfonyl Cinchona Alkaloid Amides as Organocatalysts

Authors

  • Noriyuki Hara,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5245
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  • Prof. Shuichi Nakamura,

    Corresponding author
    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5245
    • Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5245
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  • Masahide Sano,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5245
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  • Ryota Tamura,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5245
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  • Prof. Yasuhiro Funahashi,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5245
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  • Prof. Norio Shibata

    Corresponding author
    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5245
    • Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5245
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Abstract

The organocatalytic enantioselective decarboxylative addition of malonic acid half thioesters to ketimines derived from isatins by using N-heteroarenesulfonyl cinchona alkaloid amides afforded products with high enantioselectivity. The products could be converted into optically active AG-041R. X-ray crystallographic analysis revealed that the hydrogen bonding between the sulfonimide proton and the 8-quinolyl nitrogen atom plays an important role in exerting the enantioselectivity of the reaction.

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