Lec_25_26_27_28 - Unit VII Enols and Enolates Unit VII Enols and Enolates OH H2C O H3C OH CH3 H3C Keto HO H HO O H3C H3C O Me Me OH O CH2 O O CH2

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Unformatted text preview: Unit VII. Enols and Enolates Unit VII Enols and Enolates OH H2C O H3C OH CH3 H3C Keto HO H HO O H3C H3C O Me Me OH O CH2 O O CH2 OAc O O CH2 Enol CH2 OH O CH2 AcO HO OH O Me Me Me O Enolate O spongistatin 2 OMe Suggesting reading : 22.1-22.3, 22.5-22.8, 23.1-23.11, 23.13, 23.14 Suggested problems: 22.21, 22.22, 22.24-22.30, 22.32-22.35, 22.38, 22.44, 22.48, 22.49, 23.27-23.30, 23.33-23.39, 23.42-23.44, 23.47, 23.48, 23.52-60 Unit VII. Enols and Enolates Enols and Enolates A. Background 3. Intramolecular Aldol 1. Carbonyl Group 4. Pre-form enolate with LDA 2. Tautomerization 2. Claisen Condensation B. a-Substitution Reactions a. General 1. a-Halogenation of Ketones 1. Mechanism a. Base-promoted 2. Thermodynamics 1. Multiple halogenation b. Dieckmann Condensation 2. Haloform reaction c. Crossed Claisen b. Acid-catalyzed d. Useful Claisens 2. a-Alkylation 1. One reactant with no a-H a. LDA 2. Use ester and ketone b. Malonate esters e. Summary 1. Acetic acid derivatives 3. Michael Reaction 2. Acetoacetic acid esters a. General C. Condensation Reactions 1. Mechanism • Aldol Condensation 2. Thermodynamics a. Acid-catalyzed b. Examples b. Base-catalyzed 4. Robinson Annulation c. Mixed Aldol D. Biosynthesis d. Useful Aldols 1. Alternariol 1. One reactant with no a-H 2. Acetyl Co-A 2. Self-condensation 1 ...
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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