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Generation and Reactions of Oxiranyllithiums by Use of a Flow Microreactor System

Authors

  • Dr. Aiichiro Nagaki,

    1. Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University Nishikyo-ku, Kyoto, 615-8510 (Japan), Fax: (+81) 75-383-2727
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  • Eiji Takizawa,

    1. Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University Nishikyo-ku, Kyoto, 615-8510 (Japan), Fax: (+81) 75-383-2727
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  • Prof. Dr. Jun-ichi Yoshida

    Corresponding author
    1. Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University Nishikyo-ku, Kyoto, 615-8510 (Japan), Fax: (+81) 75-383-2727
    • Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University Nishikyo-ku, Kyoto, 615-8510 (Japan), Fax: (+81) 75-383-2727
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Abstract

A flow microreactor system consisting of micromixers and microtubes provides an effective reactor for the generation and reactions of aryloxiranyllithiums without decomposition by virtue of short residence time and efficient temperature control. The deprotonation of styrene oxides with sBuLi can be conducted by using the flow microreactor system at −78 or −68 °C (whereas much lower temperatures (<−100 °C) are needed for the same reactions conducted under macrobatch conditions). The resulting α-aryloxiranyllithiums were allowed to react with electrophiles in the flow microreactor system at the same temperature. The sequential introduction of various electrophiles onto 2,3-diphenyloxiranes was also achieved by using an integrated flow microreactor, which serves as a powerful system for the stereoselective synthesis of tetrasubstituted epoxides.

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