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    Lecture 11 - Dynamic Kinetic Resolution

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    JasmarB
    This document discusses kinetic resolution and dynamic kinetic resolution for separating enantiomers from a racemic mixture. Kinetic resolution uses a chiral reagent or catalyst that causes one enantiomer to react faster, achieving a maximum yield of 50%. Dynamic kinetic resolution also uses a chiral reagent to selectively remove one enantiomer through reaction. It then causes racemization of the unwanted enantiomer in situ, allowing more of it to react and achieve a maximum yield of 100%. An example is provided of applying these methods to separate enantiomers of a chiral lactone.

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    Lecture 11 - Dynamic Kinetic Resolution

    Uploaded by

    JasmarB
    119 views2 pages
    This document discusses kinetic resolution and dynamic kinetic resolution for separating enantiomers from a racemic mixture. Kinetic resolution uses a chiral reagent or catalyst that causes one enantiomer to react faster, achieving a maximum yield of 50%. Dynamic kinetic resolution also uses a chiral reagent to selectively remove one enantiomer through reaction. It then causes racemization of the unwanted enantiomer in situ, allowing more of it to react and achieve a maximum yield of 100%. An example is provided of applying these methods to separate enantiomers of a chiral lactone.

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    Resolution

    Original Title

    Lecture 11 - Dynamic Kinetic Resolution(1)

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    This document discusses kinetic resolution and dynamic kinetic resolution for separating enantiomers from a racemic mixture. Kinetic resolution uses a chiral reagent or catalyst that causes one enantiomer to react faster, achieving a maximum yield of 50%. Dynamic kinetic resolution also uses a chiral reagent to selectively remove one enantiomer through reaction. It then causes racemization of the unwanted enantiomer in situ, allowing more of it to react and achieve a maximum yield of 100%. An example is provided of applying these methods to separate enantiomers of a chiral lactone.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    119 views2 pages

    Lecture 11 - Dynamic Kinetic Resolution

    Uploaded by

    JasmarB
    This document discusses kinetic resolution and dynamic kinetic resolution for separating enantiomers from a racemic mixture. Kinetic resolution uses a chiral reagent or catalyst that causes one enantiomer to react faster, achieving a maximum yield of 50%. Dynamic kinetic resolution also uses a chiral reagent to selectively remove one enantiomer through reaction. It then causes racemization of the unwanted enantiomer in situ, allowing more of it to react and achieve a maximum yield of 100%. An example is provided of applying these methods to separate enantiomers of a chiral lactone.

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    Lecture 11 - Kinetic Resolution (KR)

    & Dynamic Kinetic Resolution (DKR)


    Kinetic Resolution
    A single enantiomer can be separated from a racemic mixture if the
    other enantiomer reacts faster with a chiral reagent or catalyst. The
    maximum yield is 50%.
    Dynamic Kinetic Resolution
    A single enantiomer can be removed from a racemic mixture if it reacts
    faster than the other enantiomer with a chiral reagent or catalyst.
    Racemisation of the unwanted isomer occurs in situ to give more of the
    reactive isomer. The maximum yield is 100%.

    Example (next page): a chiral lactone


    Note: lactones are cyclic esters
    Common (achiral) lactones:

    -propiolactone

    -butyrolactone

    GBL

    -valerolactone

    racemisation
    in situ

    chiral reducing agent


    . BH3

    - selectively reduces 1 enantiomer

    CBS catalyst

    Reduced product cannot freely rotate


    - stable atropisomer

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