Introduction of a disulfide bond as a key element of acyclic bis-thiourea-type anion receptors

    Research output: Contribution to journalArticle

    Abstract

    Two chiral porous organic polymers (CPOPs) were synthesized by linking a TADDOL-embedded building block with arylethynylenes units. The CPOPs are highly stable to thermal treatment, moisture, acidity, and basicity. The dihydroxy groups of TADDOL inside the pores promise the CPOPs as good asymmetric catalysts after postsynthesis modification with a secondary metal center. After being treated with Ti(OiPr)4, the CPOPs could be used as highly effective and reusable heterogeneous catalyst for asymmetric diethylzinc addition to aldehydes with up to 99% conversion and 95% ee. This work promises the potential of generating chiral solid catalysts with unique and practically useful enantioselective functions via a modular approach.

    Original languageEnglish
    Pages (from-to)425-434
    Number of pages10
    JournalBulletin of the Chemical Society of Japan
    Volume87
    Issue number3
    DOIs
    Publication statusPublished - Jan 1 2014

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    Thiourea
    Organic polymers
    Disulfides
    Anions
    Catalysts
    Alkalinity
    Aldehydes
    Acidity
    Moisture
    Metals
    Heat treatment

    All Science Journal Classification (ASJC) codes

    • Chemistry(all)

    Cite this

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    title = "Introduction of a disulfide bond as a key element of acyclic bis-thiourea-type anion receptors",
    abstract = "Two chiral porous organic polymers (CPOPs) were synthesized by linking a TADDOL-embedded building block with arylethynylenes units. The CPOPs are highly stable to thermal treatment, moisture, acidity, and basicity. The dihydroxy groups of TADDOL inside the pores promise the CPOPs as good asymmetric catalysts after postsynthesis modification with a secondary metal center. After being treated with Ti(OiPr)4, the CPOPs could be used as highly effective and reusable heterogeneous catalyst for asymmetric diethylzinc addition to aldehydes with up to 99{\%} conversion and 95{\%} ee. This work promises the potential of generating chiral solid catalysts with unique and practically useful enantioselective functions via a modular approach.",
    author = "Kentaro Tomita and Toshio Ishioka and Akira Harata",
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    T1 - Introduction of a disulfide bond as a key element of acyclic bis-thiourea-type anion receptors

    AU - Tomita, Kentaro

    AU - Ishioka, Toshio

    AU - Harata, Akira

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    AB - Two chiral porous organic polymers (CPOPs) were synthesized by linking a TADDOL-embedded building block with arylethynylenes units. The CPOPs are highly stable to thermal treatment, moisture, acidity, and basicity. The dihydroxy groups of TADDOL inside the pores promise the CPOPs as good asymmetric catalysts after postsynthesis modification with a secondary metal center. After being treated with Ti(OiPr)4, the CPOPs could be used as highly effective and reusable heterogeneous catalyst for asymmetric diethylzinc addition to aldehydes with up to 99% conversion and 95% ee. This work promises the potential of generating chiral solid catalysts with unique and practically useful enantioselective functions via a modular approach.

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