O-Silylated Enolates - Versatile Intermediates for Organic Synthesis

Jerald K. RASMUSSEN

doi:10.1055/s-1977-24284

Synthesis 1977; 1977(2): 91-110
DOI: 10.1055/s-1977-24284

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O-Silylated Enolates - Versatile Intermediates for Organic Synthesis

Jerald K. RASMUSSEN^*

^*Central Research Laboratories, 3M Company, P. O. Box 33221, St. Paul, Minnesota 55133, U. S. A.

Abstract

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Recent developments in the preparation and reactions of silyl enol ethers derived from aldehydes, ketones, and carboxylic acids and esters are discussed. These versatile compounds provide tremendous potential as synthetic enol equivalents. 1. Synthesis of Silyl Enol Ethers 1.1. Preparation from Enolates 1.2. Preparation from Hydrosilanes 1.3. Preparation from Other Silylating Agents 1.4. Preparation by Thermal Rearrangements 2. Synthesis of Ketene Silyl Acetals 2.1. Preparation from α-Anions and Dianions 2.2. Preparation by Hydrosilylation 3. Reactions of Silylated Enols 3.1. Preparation of Directed Enolates 3.2. Addition of Halides to the Double Bond 3.3. Reactions with Hydrogen Halides 3.4. Cycloaddition Reactions 3.5. Oxidation of Silyl Enol Ethers 3.6. Titanium(IV) Chloride Promoted Reactions 3.7. Thermal Rearrangements of Ketene Silyl Acetals 4. Conclusion

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