Parallel Kinetic Resolution of Racemic Aldehydes by Use of Asymmetric Horner-Wadsworth-Emmons Reactions

Torben Møller Pedersen, Jakob Feldthusen Jensen, Rikke Eva Humble, Tobias Rein, David Ackland Tanner, Kerstin Bodmann, Oliver Reiser

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    A racemic aldehyde can undergo parallel kinetic resolution (PKR) by simultaneous reaction with two different chiral phosphonates, differing either in the structure of the chiral auxiliary or in the structure of the phosphoryl group (i.e., one (E)- and one (Z)-selective reagent). This strategy allows conversion of a racemic aldehyde to two different, synthetically useful chiral products with essentially doubled material throughput and similar or improved selectivities as compared to conventional kinetic resolution.
    Original languageEnglish
    JournalOrganic Letters
    Volume2
    Issue number4
    Pages (from-to)535-538
    ISSN1523-7060
    DOIs
    Publication statusPublished - 2000

    Cite this

    Pedersen, Torben Møller ; Jensen, Jakob Feldthusen ; Humble, Rikke Eva ; Rein, Tobias ; Tanner, David Ackland ; Bodmann, Kerstin ; Reiser, Oliver. / Parallel Kinetic Resolution of Racemic Aldehydes by Use of Asymmetric Horner-Wadsworth-Emmons Reactions. In: Organic Letters. 2000 ; Vol. 2, No. 4. pp. 535-538.
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    title = "Parallel Kinetic Resolution of Racemic Aldehydes by Use of Asymmetric Horner-Wadsworth-Emmons Reactions",
    abstract = "A racemic aldehyde can undergo parallel kinetic resolution (PKR) by simultaneous reaction with two different chiral phosphonates, differing either in the structure of the chiral auxiliary or in the structure of the phosphoryl group (i.e., one (E)- and one (Z)-selective reagent). This strategy allows conversion of a racemic aldehyde to two different, synthetically useful chiral products with essentially doubled material throughput and similar or improved selectivities as compared to conventional kinetic resolution.",
    author = "Pedersen, {Torben M{\o}ller} and Jensen, {Jakob Feldthusen} and Humble, {Rikke Eva} and Tobias Rein and Tanner, {David Ackland} and Kerstin Bodmann and Oliver Reiser",
    year = "2000",
    doi = "10.1021/ol991387h",
    language = "English",
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    journal = "Organic Letters",
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    Pedersen, TM, Jensen, JF, Humble, RE, Rein, T, Tanner, DA, Bodmann, K & Reiser, O 2000, 'Parallel Kinetic Resolution of Racemic Aldehydes by Use of Asymmetric Horner-Wadsworth-Emmons Reactions', Organic Letters, vol. 2, no. 4, pp. 535-538. https://doi.org/10.1021/ol991387h

    Parallel Kinetic Resolution of Racemic Aldehydes by Use of Asymmetric Horner-Wadsworth-Emmons Reactions. / Pedersen, Torben Møller; Jensen, Jakob Feldthusen; Humble, Rikke Eva; Rein, Tobias; Tanner, David Ackland; Bodmann, Kerstin; Reiser, Oliver.

    In: Organic Letters, Vol. 2, No. 4, 2000, p. 535-538.

    Research output: Contribution to journalJournal articleResearchpeer-review

    TY - JOUR

    T1 - Parallel Kinetic Resolution of Racemic Aldehydes by Use of Asymmetric Horner-Wadsworth-Emmons Reactions

    AU - Pedersen, Torben Møller

    AU - Jensen, Jakob Feldthusen

    AU - Humble, Rikke Eva

    AU - Rein, Tobias

    AU - Tanner, David Ackland

    AU - Bodmann, Kerstin

    AU - Reiser, Oliver

    PY - 2000

    Y1 - 2000

    N2 - A racemic aldehyde can undergo parallel kinetic resolution (PKR) by simultaneous reaction with two different chiral phosphonates, differing either in the structure of the chiral auxiliary or in the structure of the phosphoryl group (i.e., one (E)- and one (Z)-selective reagent). This strategy allows conversion of a racemic aldehyde to two different, synthetically useful chiral products with essentially doubled material throughput and similar or improved selectivities as compared to conventional kinetic resolution.

    AB - A racemic aldehyde can undergo parallel kinetic resolution (PKR) by simultaneous reaction with two different chiral phosphonates, differing either in the structure of the chiral auxiliary or in the structure of the phosphoryl group (i.e., one (E)- and one (Z)-selective reagent). This strategy allows conversion of a racemic aldehyde to two different, synthetically useful chiral products with essentially doubled material throughput and similar or improved selectivities as compared to conventional kinetic resolution.

    U2 - 10.1021/ol991387h

    DO - 10.1021/ol991387h

    M3 - Journal article

    VL - 2

    SP - 535

    EP - 538

    JO - Organic Letters

    JF - Organic Letters

    SN - 1523-7060

    IS - 4

    ER -