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Chapter 21: Ester Enolates

Chapter 21: Ester Enolates. Fatty acid biosynthesis. carbon chain extended by 2, can go up to C16, C18, C20 iteratively. 21 – Deprotonation alpha to ester. Choice of base is important. 21 – Intermolecular acylation – the Claisen reaction. b -keto ester.

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Chapter 21: Ester Enolates

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  1. Chapter 21:Ester Enolates Fatty acid biosynthesis carbon chain extended by 2, can go up to C16, C18, C20 iteratively

  2. 21 – Deprotonation alpha to ester Choice of base is important

  3. 21 – Intermolecular acylation – the Claisen reaction b-keto ester Both enolate and ester present in mixture

  4. 21 – Examples of the Claisen reaction 2 a-H required to send reaction to the Claisen product Always need acid in second step to quench anion

  5. 21 – Intramolecular version – the Dieckmann reaction Intramolecular Claisen condensation results – cycle formed

  6. 21 – Crossed (mixed) Claisen reactions Problem: Solution:

  7. 21 – From alcohols to a,a-disubstituted ketones

  8. 21 – Examples of use

  9. 21 – The malonic ester synthesis

  10. 21 – Application in pharmaceutical (medicinal) chemistry

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